1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 59618682, compound

Participants

Reaction Steps

The title compound was prepared from 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-7-chloro-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 64) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole according to the procedure of Example 495. Racemic mixture: LC/MS: m/e 576.1 (M+H)+; 1H NMR (500 MHz, CD3OD): δ 8.05 (1H, s), 7.80 (1H, s), 7.58 (1H, d), 7.41 (2H, d), 7.10 (3H, m), 7.05 (1H, d), 7.00-7.10 (2H, d), 5.19 (1H, d), 5.55 (1H, d), 3.96 (3H, s), 1.26 (9H, s). The racemic mixture was separated on a Chiracel OD-H column eluting with 20% EtOH in hexanes at 8.0 mL/min. The faster eluting enantiomer E1 had a retention time of 40 min. The slower eluting enantiomer E2 had a retention time of 50 min.

Provenance & Evidence