Dimethylformamide → HCID 131733230, compound

Participants

Reaction Steps

Following a procedure similar to the one in Example 36, 1-(4-chlorophenyl)-4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (100 mg, 0.251 mmol), 4-(methanesulfonyl)bromobenzene (76 mg, 0.301 mmol), cesium carbonate (245 mg, 0.752 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (20 mg, 0.0251 mmol) in DMF (2.0 mL) and water (0.5 mL) gave the desired product (11.2 mg, 11%) as a colorless oil. To a solution of the benzodiazepine (11.2 mg, 0.026 mmol) in methanol (1 mL) and water (3 mL) was added L-tartaric acid (4.1 mg, 0.026 mmol) and the resultant solution was lyophilized overnight to give 1-(4-chlorophenyl)-4-methyl-7-(4-(methylsulfonyl)phenyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine, L-tartrate salt (15.0 mg, 98%, AUC HPLC>99%) as a yellow solid: 1H NMR (CD3OD, 500 MHz) δ 8.04 (d, J=8.3 Hz, 2H), 7.92 (d, J=8.4 Hz, 2H), 7.88 (s, 1H), 7.76 (d, J=8.3 Hz, 1H), 7.28 (d, J=8.3 Hz, 1H), 7.22 (d, J=9.0 Hz, 2H), 6.89 (d, J=8.9 Hz, 2H), 4.43 (s, 1H), 4.21 (s, 2H), 3.96 (bs, 2H), 3.44 (bs, 2H), 3.17 (s, 3H), 2.84 (s, 3H); ESI MS m/z 427 [M+H]+.

Provenance & Evidence