Example 280
To a solution of 2-chloro-1-(3-(2-(3,4-dimethoxyphenyl)-3-isopropyl-1H-indol-5-yl)-7-azabicyclo[4.1.1]octan-7-yl)ethanone (0.11 g, 0.229 mmol) in THF (2 mL) was added DIPEA (0.080 mL, 0.457 mmol) and dimethylamine (0.172 mL, 0.343 mmol) in THF. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with EtOAc (10 mL), washed with water (2×20 mL), dried over sodium sulphate, and concentrated to afford crude product. The crude material was purified by Preparative LCMS using method D2, the fractions containing the product was collected and concentrated to afford 1-(3-(2-(3,4-dimethoxyphenyl)-3-isopropyl-1H-indol-5-yl)-7-azabicyclo[4.1.1]octan-7-yl)-2-(dimethylamino)ethanone (1.5 mg, 1.34%). LCMS retention time 1.45 min (F). MS m/z: 490.4 (M+H). 1H NMR (400 MHz, DMSO-de) δ ppm 10.80 (s, 1H), 7.51 (s, 1H), 7.23 (d, J=8.5 Hz, 1H), 7.11-7.04 (m, 2H), 7.03-6.99 (m, 1H), 6.96 (dd, J=8.3, 1.8 Hz, 1H), 3.82 (d, J=7.0 Hz, 4H), 3.31 (d, J=7.0 Hz, 2H), 3.02-2.93 (m, 2H), 2.90 (s, 6H), 2.26-2.16 (m, 4H), 1.74-1.64 (m, 4H), 1.56-1.50 (m, 2H), 1.46 (d, J=11.0 Hz, 2H), 1.41 (d, J=7.0 Hz, 6H).
