Dimethyl Sulfoxide → 6-[(4-tert-Butylphenyl)sulfonyl]-8-(1-methyl-1H-pyrazol-4-yl)-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 53, 50 mg, 0.0925 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (38.5 mg, 0.185 mmol), Pd(dppf)Cl2 (22.7 mg, 0.0278 mmol), potassium carbonate (38.4 mg, 0.2775 mmol), DMSO (0.3 mL), and 3 drops of water was heated in a microwave reactor at 100° C. for 30 min. After cooling to room temperature, the reaction mixture was diluted with EtOAc, and the organic layer was separated, washed with water, brine, dried over MgSO4 and concentrated. The residue was purified via reverse phase HPLC to provide the title compound. LC/MS: m/e 542.0 (M+H)+. 1H NMR (500 MHz, CD3OD): δ 7.93 (1H, s), 7.78 (1H, s), 7.60 (2H, m), 7.40 (1H, d), 7.16 (2H, d), 7.05 (1H, d), 6.95 (1H, d), 6.90 (2H, d), 4.60-5.00 (2H, br s), 3.90 (3H, s), 1.26 (9H, s).

Provenance & Evidence