Methanol → HCID 66901654, compound

Participants

Reaction Steps

To a solution of 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (0.168 g, 0.32 mmol, intermediate 53) in DMF (2.0 mL) under nitrogent (balloon) was added palladium acetate (0.072 g, 0.32 mmol), dppf (0.220 g, 0.40 mmol), triethylamine (0.080 g, 0.800 mmol), and methanol (2.0 mL). The nitrogen balloon was replaced with a carbon monoxide balloon and the reaction mixture was stirred at rt for 1 h, and at 80° C. for 15 h. After cooling to rt, the reaction mixture was diluted with EtOAc and filtered through a pad of silica gel. The filtrate was concentrated to dryness and the residue was purified by SiO2 column chromatography eluting with EtOAc in hexanes to provide the title compound. LC/MS: m/e 520.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.28 (1H, d, J=1.6 Hz), 7.94 (1H, dd, J=8.5, 1.8 Hz), 7.61 (1H, d, J=7.5 Hz), 7.13 (1H, d, J=7.6 Hz), 7.10 (2H, d, J=8.5 Hz), 6.99 (1H, s), 6.92 (2H, d, J=8.4 Hz), 6.80 (1H, m), 4.70-4.90 (2H, br), 3.95 (3H, s), 1.25 (9H, s).

Provenance & Evidence