Lithium Chloride → HCID 59618815, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (270 mg, 0.5 mmol, from intermediate 53, Pd(dppf)Cl2 (165 mg, 0.2 mmol), and LiCl (21 mg, 0.5 mmol) were dissolved in NMP (1.5 mL) under N2 was added tri-n-butyl(1-ethoxyvinyl)tin (180 mg, 0.5 mmol), and the resulting mixture was stirred at 90° C. for 1 h. The cooled reaction mixture was poured into 1M HCl/Et2O (5 mL) and stirred vigorously for 2 h. The product was extracted with EtOAc and the combined extracts were washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by SiO2 column chromatography to provide the title compound. LC/MS: m/e 504.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.19 (1H, s), 7.92 (1H, d, J=8.4 Hz), 7.64 (1H, d, J=7.6 Hz), 7.15 (1H, d, J=7.5 Hz), 7.12 (2H, d, J=8.4 Hz), 7.01 (1H, s), 6.94 (2H, d, J=8.2 Hz), 6.83 (1H, d, J=8.4 Hz), 4.65-4.9 (2H, br), 2.64 (3H, s), 1.25 (9H, s).

Provenance & Evidence