Pyridine → 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Participants

Reaction Steps

A solution of 8-bromo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (5.16 g, 15 mmol, intermediate 36), (4-tert-butylphenyl)sulfonyl chloride (10.5 g, 45 mmol), pyridine (7.11 g, 90 mmol), DMAP (0.366 g, 3 mmol in DCM (75 mL) was stirred at rt for 24 h. The reaction was quenched with water, and the product was extracted with EtOAc (3×). The combined extracts were washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was recrystallized from DCM and hexanes to afford the title compound. LC/MS: m/e 542.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.76 (1H, d, J=2.3 Hz), 7.56 (1H, d, J=7.3 Hz), 7.36 (1H, dd, J=8.7, 2.3 Hz), 7.11 (2H, d, J=8.5 Hz), 7.09 (1H, d, J=7.5 Hz), 6.96 (2H, d, J=8.4 Hz), 6.72 (1H, s), 6.62 (1H, d, J=8.7 Hz), 4.70-4.90 (2H, br), 1.25 (9H, s).

Provenance & Evidence