General procedure for the synthesis of 1-(2-nitrophenyl)-N-phenylmethanimines (
2–
6). 2-Nitrobenzaldehyde (5 g, 33.08 mmol) and aniline or the corresponding substituted aniline (33.08 mmol, 1 eq) were dissolved in ethanol (12–40 mL; the minimum quantity to dissolve the starting materials) and stirred at reflux temperature for 1–4 h to yield compounds
2–
4,
6. Finally, the mixture was cooled to induce crystallization and the solid formed was separated using vacuum filtration and washed with cold ethanol. This same reaction was carried out at room temperature to yield compound
5.
General procedure for the synthesis of 2-phenyl-2H-indazole derivatives (
7–
11). 2-Phenyl-2
H-indazole derivatives were synthesized employing a slight modification of the Cadogan method [24 (
link)]. The corresponding imine
2–
6 (20 mmol) was heated in triethyl phosphite (60 mmol) at 150 °C (0.5–2 h) until the starting material was totally consumed. Then, phosphite and phosphate were separated using vacuum distillation and the residue was purified using column chromatography with hexane–ethyl acetate (90:10) as a mobile phase to give the respective 2-phenyl-2
H-indazole derivatives
7–
9 and
11. A slightly more polar mobile phase was used for the purification of the compound
10, hexane-ethyl acetate (80:20).
4-(2H-indazol-2-yl) phenol (
12). Compound
9 (4 mmol) was dissolved in dichloromethane (12 mL) and cooled to 0 °C under N
2 atmosphere. Then, boron tribromide (12 mL of 1 M solution in dichloromethane, 12 mmol) was added and the reaction mixture was warmed to room temperature and stirred overnight. After completion of the reaction, a saturated sodium bicarbonate solution was added and the solid formed was filtered under vacuum. The crude product was purified using a short column packed with silica gel and ethyl acetate-hexanes (6:4) as a mobile phase to give compound
12.
General procedure for the synthesis of derivatives13,
20, and25. The appropriate methyl ester derivative (
10,
18, and
23, 1.2 mmol) was dissolved in methanol (7.5 mL) and an aqueous solution of NaOH (3.6 mmol in 3 mL of water) was added. The reaction mixture was heated under reflux for five hours. After completion of the reaction, the mixture was cooled on ice and acidified to pH 1 with HCl to induce precipitation. The solid was separated using vacuum filtration and dried.
2-(4-(Methylsulfinyl) phenyl)-2H-indazole (
14). To a solution of compound
11 (0.8 mmol) in 28 mL of CH
3CN/CH
3COOH (1:1), NaIO
4 (0.8 mmol) dissolved in 2 mL of H
2O/AcOH (4:1) was added. The reaction mixture was stirred at room temperature for 24 h. Then, the reaction was neutralized with a saturated solution of sodium bicarbonate and the product was extracted with dichloromethane (3 × 50 mL). The organic phase was dried with anhydrous sodium sulfate and concentrated under vacuum. The evaporation residue was purified by column chromatography using dichloromethane/methanol (98:2) as a mobile phase to give compound
14.
General procedure for the synthesis of derivatives15,
21, and
26. NaIO
4 (5 mmol) dissolved in 5 mL of H
2O/AcOH (4:1) were added to a solution of the proper indazole derivative
11,
19, or
24 (2 mmol) in 28 mL of CH
3CN/CH
3COOH (1:1). The reaction mixture was stirred at reflux temperature for 12 h. Then, the mixture was neutralized with a saturated solution of sodium bicarbonate and brine solution was added until complete precipitation. The solid was separated using vacuum filtration and dried. The crude product was purified by column chromatography using dichloromethane as a mobile phase.
General procedure for the synthesis of 2,3-diphenyl-2H-indazole derivatives16–
19 and
22–
24. Compounds
16–
19 and
22–
24 were synthesized by a palladium catalyzed arylation as previously described by Ohnmacht et al. [27 (
link)]. It is worth mentioning that the previously-reported methodology was scaled up to 0.5 g of starting 2-phenyl-2
H-indazole. Whereas compounds
16–
19,
22, and
23, were synthesized using the proper 2-phenyl-2
H-indazole and the substituted 4-iodobenzene, only compound
24 was synthesized from 2-phenyl-2
H-indazole and 4-bromothioanisole.
1-(2-Nitrophenyl)-N-phenylmethanimine (
2). Yellow solid (93% yield); m.p.: 64.1–64.9 °C (lit [24 (
link)]: 63–64 °C);
1H-NMR (600 MHz, CDCl
3) δ 8.94 (s, 1H), 8.31 (dd,
J = 7.8, 1.4 Hz, 1H), 8.07 (dd,
J = 8.2, 1.1 Hz, 1H), 7.74 (t,
J = 7.6 Hz, 1H), 7.64–7.60 (m, 1H), 7.45–7.40 (m, 2H), 7.31–7.27 (m, 3H);
13C-NMR (151 MHz, CDCl
3) δ 155.84, 151.07, 149.34, 133.58, 131.18, 131.12, 129.75, 129.28, 126.92, 124.54, 121.18.
N-(4-Chlorophenyl)-1-(2-nitrophenyl) methanimine (
3). Dark yellow solid (91% yield); m.p.: 91.2–92.2 °C (lit [36 (
link)]: 91–92 °C).
1H-NMR (600 MHz, CDCl
3) δ 8.93 (s, 1H), 8.29 (dd,
J = 7.8, 1.5 Hz, 1H), 8.08 (dd,
J = 8.2, 1.2 Hz, 1H), 7.78–7.72 (m, 1H), 7.67–7.61 (m, 1H), 7.41–7.36 (m, 2H), 7.25–7.20 (m, 2H);
13C-NMR (151 MHz, CDCl
3) δ 156.24, 149.49, 149.32, 133.64, 132.58, 131.40, 130.87, 129.72, 129.40, 124.61, 122.54.
N-(4-Methoxyphenyl)-1-(2-nitrophenyl) methanimine (
4). Yellow solid (92% yield); m.p.: 79.1–79.9 °C (lit [36 (
link)]: 81–82 °C);
1H-NMR (600 MHz, CDCl
3) δ 8.97 (s, 1H), 8.32 (dd,
J = 7.8, 1.4 Hz, 1H), 8.06 (dd,
J = 8.2, 1.1 Hz, 1H), 7.75–7.70 (m, 1H), 7.62–7.57 (m, 1H), 7.35–7.29 (m, 2H), 6.98–6.94 (m, 2H), 3.85 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 159.09, 153.31, 143.88, 133.48, 131.36, 130.81, 129.55, 124.53, 122.78, 114.50, 55.53.
Methyl 4-((2-nitrobenzylidene) amino)benzoate (
5) Pale yellow solid (73% yield); m.p.: 122.7–124.4 °C;
1H-NMR (600 MHz, CDCl
3) δ 8.93 (s, 1H), 8.30 (dd,
J = 7.7, 1.0 Hz, 1H), 8.10 (d,
J = 8.4 Hz, 3H), 7.76 (t,
J = 7.6 Hz, 1H), 7.68–7.63 (m, 1H), 7.30–7.25 (m, 2H), 3.93 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 166.66, 157.50, 155.14, 149.39, 133.71, 131.66, 130.95, 130.70, 129.84, 128.26, 124.65, 120.93, 52.15; MS (HR-ESI) for C
15H
12N
2O
4 [M + H]
+, calcd:
m/
z 285.0870, found:
m/
z 285.0861.
N-(4-(Methylthio)phenyl)-1-(2-nitrophenyl)methanimine (
6). Burnt orange solid (92% yield); m.p.: 69.3–70.4 °C;
1H-NMR (600 MHz, CDCl
3) δ 8.96 (s, 1H), 8.31 (dd,
J = 7.8, 1.4 Hz, 1H), 8.07 (dd,
J = 8.2, 1.1 Hz, 1H), 7.73 (t,
J = 7.5 Hz, 1H), 7.63–7.58 (m, 1H), 7.33–7.22 (m, 4H), 2.52 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 154.86, 149.25, 148.06, 137.45, 133.51, 131.07, 129.63, 127.37, 124.53, 121.89, 16.06; MS (HR-ESI) for C
14H
12N
2O
2S [M + H]
+, calcd:
m/
z 273.0692, found:
m/
z 273.0683.
2-Phenyl-2H-indazole (
7). White solid (64% yield); m.p.: 81.2–81.6 °C (lit [24 (
link)]: 81–82 °C); the spectroscopic data matched previously reported data [37 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 8.40 (d,
J = 0.9 Hz, 1H), 7.91–7.88 (m, 2H), 7.79 (dd,
J = 8.8, 0.9 Hz, 1H), 7.70 (dt,
J = 8.5, 1.0 Hz, 1H), 7.54–7.50 (m, 2H), 7.41–7.37 (m, 1H), 7.32 (ddd,
J = 8.8, 6.6, 1.0 Hz, 1H), 7.11 (ddd,
J = 8.4, 6.6, 0.7 Hz, 1H);
13C-NMR (151 MHz, CDCl
3) δ (ppm): 149.78, 140.52, 129.54, 127.88, 126.81, 122.76, 122.44, 120.99, 120.39, 120.37, 117.94.
2-(4-Chlorophenyl)-2H-indazole (
8). White solid (57% yield); m.p.: 143.0–145.5 °C (lit [38 (
link)]: 138–140 °C); the spectroscopic data matched previously reported data [38 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 8.37 (d,
J = 1.0 Hz, 1H), 7.87–7.82 (m, 2H), 7.77 (dq,
J = 8.8, 0.9 Hz, 1H), 7.69 (dt,
J = 8.5, 1.0 Hz, 1H), 7.51–7.47 (m, 2H), 7.33 (ddd,
J = 8.8, 6.6, 1.1 Hz, 1H), 7.12 (ddd,
J = 8.5, 6.6, 0.8 Hz, 1H);
13C-NMR (151 MHz, CDCl
3) δ 149.89, 139.02, 133.55, 129.67, 127.09, 122.87, 122.71, 122.00, 120.29, 117.90.
2-(4-Methoxyphenyl)-2H-indazole (
9). Beige solid (56 % yield); m.p.: 133.2–135.8 °C (lit [39 ]: 130–131 °C); the spectroscopic data matched previously reported data [40 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 8.30 (d,
J = 0.9 Hz, 1H), 7.82–7.76 (m, 3H), 7.69 (dt,
J = 8.4, 1.0 Hz, 1H), 7.31 (ddd,
J = 8.7, 6.6, 1.0 Hz, 1H), 7.10 (ddd,
J = 8.4, 6.6, 0.8 Hz, 1H), 7.05–6.99 (m, 2H), 3.86 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 159.28, 149.58, 134.12, 126.53, 122.70, 122.41, 122.22, 120.30, 120.25, 117.77, 114.63, 55.60.
Methyl 4-(2H-indazol-2-yl) benzoate (
10). White solid (52% yield); m.p.: 185.8–186.2 °C (lit [41 ]: 186–187 °C); the spectroscopic data matched previously reported data [40 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 8.47 (d,
J = 0.7 Hz, 1H), 8.22–8.18 (m, 2H), 8.02–7.99 (m, 2H), 7.77 (dd,
J = 8.8, 0.8 Hz, 1H), 7.69 (d,
J = 8.5 Hz, 1H), 7.33 (ddd,
J = 8.8, 6.6, 1.0 Hz, 1H), 7.14–7.10 (m, 1H), 3.95 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 166.19, 150.19, 143.64, 131.16, 129.27, 127.45, 123.01, 122.98, 120.47, 120.26, 118.06, 52.33.
2-(4-(Methylthio) phenyl)-2H-indazole (
11). Pale yellow solid (61% yield); m.p.: 148.3–149.7 °C (lit [38 (
link)]: 137–139 °C); the spectroscopic data matched previously reported data [38 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 8.35 (d,
J = 0.8 Hz, 1H), 7.84–7.80 (m, 2H), 7.79–7.76 (m, 1H), 7.68 (dt,
J = 8.5, 0.9 Hz, 1H), 7.39–7.35 (m, 2H), 7.31 (ddd,
J = 8.7, 6.6, 1.0 Hz, 1H), 7.10 (ddd,
J = 8.4, 6.6, 0.8 Hz, 1H), 2.53 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 149.72, 138.63, 137.78, 127.27, 126.82, 122.77, 122.46, 121.26, 120.30, 120.12, 117.84, 15.88.
4-(2H-Indazol-2-yl) phenol (
12). Beige solid (64% yield); m.p.: 179–181 °C (lit [25 (
link)]: 193–194 °C); the spectroscopic data matched previously reported data [42 ]:
1H-NMR (600 MHz, DMSO-
d6) δ 9.85 (s, 1H), 8.91 (d,
J = 0.9 Hz, 1H), 7.91–7.84 (m, 2H), 7.75 (dt,
J = 8.4, 1.0 Hz, 1H), 7.69 (dq,
J = 8.8, 0.9 Hz, 1H), 7.29 (ddd,
J = 8.7, 6.6, 1.1 Hz, 1H), 7.08 (ddd,
J = 8.3, 6.6, 0.8 Hz, 1H), 6.98–6.92 (m, 2H);
13C-NMR (151 MHz, DMSO-
d6) δ 157.09, 148.47, 132.11, 126.10, 122.24, 121.75, 121.57, 120.78, 120.58, 117.12, 115.81.
4-(2H-Indazol-2-yl) benzoic acid (
13). White solid (96% yield); m.p.: 288.3–288.5 °C (lit [41 ]: 286–288 °C);
1H-NMR (600 MHz, DMSO-
d6) δ 9.23 (s, 1H), 8.29–8.23 (m, 2H), 8.18–8.12 (m, 2H), 7.79 (dt,
J = 8.5, 1.0 Hz, 1H), 7.73 (dq,
J = 8.8, 0.9 Hz, 2H), 7.35 (ddd,
J = 8.8, 6.5, 1.1 Hz, 1H), 7.13 (ddd,
J = 8.5, 6.6, 0.8 Hz, 1H);
13C-NMR (151 MHz, DMSO-
d6) δ 166.46, 149.22, 142.83, 130.82, 129.65, 127.28, 122.54, 122.43, 122.04, 120.99, 119.86, 117.48.
2-(4-(Methylsulfinyl) phenyl)-2H-indazole (
14). White solid (92% yield); m.p.: 150.1–152.7 °C;
1H-NMR (600 MHz, CDCl
3) δ 8.47 (d,
J = 0.9 Hz, 1H), 8.13–8.07 (m, 2H), 7.83–7.75 (m, 3H), 7.70 (dt,
J = 8.5, 1.0 Hz, 1H), 7.34 (ddd,
J = 8.8, 6.6, 1.1 Hz, 1H), 7.13 (ddd,
J = 8.5, 6.6, 0.8 Hz, 1H), 2.78 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 150.14, 145.05, 142.47, 127.45, 125.03, 123.01, 121.49, 120.46, 120.43, 118.01, 44.10; MS (HR-ESI) for C
14H
12N
2OS [M + Na]
+, calcd:
m/
z 279.0562, found:
m/
z 279.0481.
2-(4-(Methylsulfonyl) phenyl)-2H-indazole (
15). White solid (68% yield); m.p.: 200.6–201.5 °C;
1H-NMR (600 MHz, CDCl
3) δ 8.50 (d,
J = 0.8 Hz, 1H), 8.19–8.05 (m, 4H), 7.76 (m, 1H), 7.70 (m, 1H), 7.35 (ddd,
J = 8.8, 6.6, 1.0 Hz, 1H), 7.14 (ddd,
J = 8.5, 6.6, 0.7 Hz, 1H), 3.11 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 150.43, 144.23, 139.27, 129.18, 127.87, 123.36, 123.18, 120.99, 120.57, 120.54, 118.11, 44.62; MS (HR-ESI) for C
14H
12N
2O
2S [M + H]
+, calcd:
m/
z 273.0692, found:
m/
z 273.0659.
2,3-Diphenyl-2H-indazole (
16). White solid (77% yield); mp: 107.4–107.9 °C (lit [27 (
link)]: 102–103 °C);
1H-NMR (600 MHz, CDCl
3) δ 7.82–7.79 (m, 1H), 7.73–7.70 (m, 1H), 7.45–7.42 (m, 2H), 7.41–7.34 (m, 9H), 7.14 (ddd,
J = 8.4, 6.6, 0.8 Hz, 1H);
13C-NMR (151 MHz, CDCl
3) δ 148.99, 140.24, 135.41, 129.91, 129.69, 128.97, 128.76, 128.30, 128.25, 126.98, 126.02, 122.50, 121.74, 120.52, 117.76.
2-(4-Chlorophenyl)-3-phenyl-2H-indazole (
17). White solid (45% yield); m.p.: 124.4–125.0 °C (lit [43 (
link)]: 126 °C);
1H-NMR (600 MHz, CDCl
3) δ 7.78 (dt,
J = 8.8, 0.9 Hz, 1H), 7.68–7.69 (dt,
J = 8.5, 0.9 Hz, 1H), 7.45–7.32 (m, 10H), 7.14 (ddd,
J = 8.4, 6.6, 0.8 Hz, 1H);
13C-NMR (151 MHz, CDCl
3) δ 149.12, 138.75, 135.47, 134.09, 129.67, 129.63, 129.18, 128.94, 128.55, 127.26, 127.10, 122.73, 121.86, 120.49, 117.72; MS (HR-ESI) for C
19H
13ClN
2 [M + H]
+, calcd:
m/
z 305.0840, found:
m/
z 305.0736.
Methyl 4-(3-phenyl-2H-indazol-2-yl) benzoate (
18). Pale yellow solid (40% yield); m.p.: 152.4–154.9 °C;
1H-NMR (600 MHz, CDCl
3) δ 8.07–8.04 (m, 2H), 7.80 (dt,
J = 8.8, 0.8 Hz, 1H), 7.69 (dt,
J = 8.6, 1.0 Hz, 1H), 7.55–7.52 (m, 2H), 7.44–7.34 (m, 6H), 7.15 (ddd,
J = 8.5, 6.6, 0.8 Hz, 1H), 3.93 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 166.21, 149.34, 143.76, 135.69, 130.42, 129.70, 129.62, 128.98, 128.66, 127.46, 125.69, 122.89, 122.08, 120.53, 117.81, 52.33; MS (HR-ESI) for C
21H
16N
2O
2 [M + H]
+, calcd:
m/
z 329.1285, found:
m/
z 329.1103.
2-(4-(Methylthio) phenyl)-3-phenyl-2H-indazole (
19). Pale yellow solid (71% yield) m.p.: 87.7–89.0 °C;
1H-NMR (600 MHz, CDCl
3) δ 7.79 (dt,
J = 8.9, 1.0 Hz, 1H), 7.70 (dt,
J = 8.6, 1.0 Hz, 1H), 7.43–7.34 (m, 8H), 7.24–7.21 (m, 2H), 7.13 (ddd,
J = 8.4, 6.6, 0.8 Hz, 1H), 2.49 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 148.97, 139.16, 137.23, 135.26, 129.88, 129.68, 128.83, 128.35, 127.00, 126.40, 126.19, 122.50, 121.78, 120.46, 117.68, 15.58; MS (HR-ESI) for C
20H
16N
2S [M + H]
+, calcd:
m/
z 317.1107, found:
m/
z 317.1108.
4-(3-Phenyl-2H-indazol-2-yl) benzoic acid (
20). White solid (70% yield); m.p.: 129.2–130.1 °C;
1H-NMR (600 MHz, DMSO-
d6) δ 8.04–7.99 (m, 2H), 7.77 (d,
J = 8.8 Hz, 1H), 7.69 (d,
J = 8.5 Hz, 1H), 7.59–7.55 (m, 2H), 7.51–7.37 (m, 6H), 7.18 (dd,
J = 8.4, 6.6 Hz, 1H);
13C-NMR (151 MHz, DMSO-
d6) δ 166.41, 148.44, 143.00, 135.18, 130.45, 130.07, 129.44, 128.95, 128.87, 128.63, 127.18, 125.91, 122.73, 121.30, 120.32, 117.41; MS (HR-ESI) for C
20H
14N
2O
2 [M + H]
+, calcd:
m/
z 315.1128, found:
m/
z 315.1142.
2-(4-(Methylsulfonyl) phenyl)-3-phenyl-2H-indazole (
21). Pale yellow solid (77% yield), m.p.: 101.8–102.7 °C;
1H-NMR (600 MHz, CDCl
3) δ 7.98–7.94 (m, 2H), 7.78 (dt,
J = 8.9, 0.8 Hz, 1H), 7.70–7.66 (m, 3H), 7.48–7.42 (m, 3H), 7.39 (ddd,
J = 8.8, 6.5, 1.0 Hz, 1H), 7.38–7.35 (m, 2H), 7.16 (ddd,
J = 8.4, 6.5, 0.7 Hz, 1H), 3.08 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 149.58, 144.52, 139.70, 135.94, 129.70, 129.28, 129.23, 129.00, 128.41, 127.85, 126.45, 123.23, 122.29, 120.58, 117.81, 44.52; MS (HR-ESI) for C
20H
16N
2O
2S [M + H]
+, calcd:
m/
z 349.1005, found:
m/
z 349.1005.
3-(4-Chlorophenyl)-2-phenyl-2H-indazole (
22). White solid (67% yield); m.p.: 141.1–142.8 °C (lit [27 (
link)]: 134–135 °C); the spectroscopic data matched previously reported data [27 (
link),44 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 7.80 (dt,
J = 8.8, 0.8 Hz, 1H), 7.67 (dt,
J = 8.6, 1.0 Hz, 1H), 7.44–7.35 (m, 8H), 7.30–7.27 (m, 2H), 7.16 (ddd,
J = 8.4, 6.5, 0.7 Hz, 1H);
13C-NMR (151 MHz, CDCl
3) δ 149.00, 139.98, 134.45, 134.08, 130.84, 129.14, 129.12, 128.48, 128.38, 127.08, 126.01, 122.86, 121.71, 120.11, 117.91.
Methyl 4-(2-phenyl-2H-indazol-3-yl) benzoate (
23). Pale yellow solid (76% yield): m.p.: 164.5–166.3 °C; the spectroscopic data matched previously reported data [45 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 8.08–8.04 (m, 2H), 7.84–7.80 (m, 1H), 7.72 (dt,
J = 8.5, 0.9 Hz, 1H), 7.45–7.37 (m, 8H), 7.19 (ddd,
J = 8.5, 6.5, 0.6 Hz, 1H), 3.93 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 166.55, 149.08, 139.99, 134.37, 134.13, 129.97, 129.66, 129.49, 129.18, 128.59, 127.14, 126.04, 123.18, 121.90, 120.09, 118.02, 52.29.
3-(4-(Methylthio) phenyl)-2-phenyl-2H-indazole (
24). White solid, (36% yield); m.p.: 119.3–121.4 °C; the spectroscopic data matched previously reported data [45 (
link)]:
1H-NMR (600 MHz, CDCl
3) δ 7.79 (dt,
J = 8.8, 0.9 Hz, 1H), 7.70 (dt,
J = 8.5, 1.0 Hz, 1H), 7.46–7.43 (m, 2H), 7.42–7.34 (m, 4H), 7.29–7.23 (m, 4H), 7.14 (ddd,
J = 8.5, 6.6, 0.8 Hz, 1H), 2.50 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 149.01, 140.22, 139.32, 134.94, 129.90, 129.06, 128.29, 126.99, 126.27, 126.16, 126.02, 122.50, 121.66, 120.43, 117.80, 15.26.
4-(2-Phenyl-2H-indazol-3-yl) benzoic acid (
25). White solid (87% yield); mp: 296.2–298.2 °C;
1H-NMR (600 MHz, DMSO-
d6) δ 7.94–7.90 (m, 2H), 7.75 (d,
J = 8.7 Hz, 1H), 7.71 (d,
J = 8.5 Hz, 1H), 7.49–7.42 (m, 5H), 7.38 (ddd,
J = 8.7, 6.6, 0.9 Hz, 1H), 7.30–7.26 (m, 2H), 7.16 (ddd,
J = 8.4, 6.6, 0.6 Hz, 1H);
13C-NMR (151 MHz, DMSO-
d6) δ 169.13, 148.11, 140.15, 139.79, 135.10, 129.32, 129.17, 128.98, 128.37, 128.26, 126.77, 125.88, 122.34, 121.02, 120.38, 117.29; MS (HR-ESI) for C
20H
14N
2O
2 [M + H]
+, calcd:
m/
z 315.1128, found:
m/
z 315.1139.
3-(4-(Methylsulfonyl) phenyl)-2-phenyl-2H-indazole (
26). Pale yellow solid (60% yield), mp: 206.9–208.8 °C;
1H-NMR (600 MHz, CDCl
3) δ 7.98–7.94 (m, 2H), 7.84 (dt,
J = 8.7, 0.9 Hz, 1H), 7.71 (dt,
J = 8.5, 1.0 Hz, 1H), 7.57–7.54 (m, 2H), 7.45–7.39 (m, 6H), 7.22 (ddd,
J = 8.5, 6.6, 0.9 Hz, 1H), 3.11 (s, 3H);
13C-NMR (151 MHz, CDCl
3) δ 149.10, 139.83, 139.71, 135.46, 132.95, 130.24, 129.40, 128.90, 127.86, 127.27, 126.06, 123.70, 122.03, 119.64, 118.22, 44.42; MS (HR-ESI) for C
20H
16N
2O
2S [M + H]
+, calcd:
m/
z 349.1005, found:
m/
z 349.1005.
Pérez-Villanueva J., Yépez-Mulia L., González-Sánchez I., Palacios-Espinosa J.F., Soria-Arteche O., Sainz-Espuñes T.D., Cerbón M.A., Rodríguez-Villar K., Rodríguez-Vicente A.K., Cortés-Gines M., Custodio-Galván Z, & Estrada-Castro D.B. (2017). Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents. Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, 22(11), 1864.