Dimethylformamide → HCID 24828472, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (89.7 mg, 0.20 mmol), 1-bromo-3-nitro-benzene (41.3 mg, 0.20 mmol), and Pd[P(Ph)3]4 (15.5 mg, 6.7 mol %) in methanol (2 mL), NaHCO3 (sat. aq., 300 μL), and DMF (400 μL) was degassed and heated to 70° C. overnight in a sealed vial. The reaction was cooled, filtered, and purified by reverse phase HPLC to give the desired product. Yield 7.0 mg. MS: 446.1 (M+H+); H1 NMR (DMSO-d6): δ (ppm) 1.77-2.04 (m, 3H), 2.16-2.47 (m, 1H), 3.38-3.60 (m, 2H), 4.32-4.42 (m, 1H), 4.90-5.13 (m, 2H), 7.02-8.38 (m, 13H), 10.15-10.23 (s, 1H).

Provenance & Evidence