Dichloromethane → HCID 20746008, compound

Participants

Reaction Steps

To a stirred solution of [7-(4-Fluoro-2-methyl-1 h-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-(3-methoxy-pyrrolidin-1-yl)-methanone (399 mg, 0.94 mmole) in CH2Cl2 (30 ml) and DMSO (0.2 ml) were added, sequentially, freshly crushed NaOH (700 mg, 17.50 mmole), Bu4NBr (25 mg, catalytic amount) and 4-nitrophenyl chloroformate (1.18 g, 5.84 mmole). After stirring at ambient temperature for overnight, the reaction mixture was filtered and the filtrate was concentrated, in vacuo, to give crude product, which was further purified by flash column chromatography eluted with EtOAc : CH2Cl2:MeOH (1:1:0.02) to provide 110 mg (19%) of a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.55 (1H, d, J=5.5 Hz), 8.40 (2H, d, J=8.7 Hz), 8.04 (1H, d, J=9.1 Hz), 7.86 (1H, d, J=10.7 Hz), 7.53 (2H, d, J=9.04 Hz), 7.26 (1H, dd, J=9.2, 1.9 Hz), 6.62 (1H, d, J=5.5 Hz), 4.02-3.89 (3H, m), 3.88-3.71 (2H, m), 3.37 (3H, d, J=15.1 Hz), 2.73 (3H, s), 2.29-2.08 (2H, m).

Provenance & Evidence