Sodium Bicarbonate → (S)-tert-butyl 2-(5-(4'-(2-acetamido-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(5-(4-bromophenyl)-1H-imidazol-2-yl)acetamide (0.604 g, 2.16 mmol), (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (0.950 g, 2.16 mmol), NaHCO3 (0.636 g, 7.57 mmol) in DME (20 mL) and H2O (5 mL) was degassed by evacuating and back-filling with N2 (×3). To this solution Pd(PPh3)4 (0.125 g, 0.11 mmol) was added and the suspension heated at 125° C. for 24 h. The mixture was evaporated to dryness in vacuo and the residue was purified by column chromatography (Biotage) eluting with a gradient of 0 to 10% MeOH in CH2C2. The material was then purified by prep HPLC (CH3CN—H2O—NH4OAc) to afford the title compound as a colorless solid. 7.76 (app dd, J=8.4, 2.2 Hz, 4H), 7.69 (app d, J=8.4 Hz, 2H), 7.66 (app d, J=8.4 Hz, 2H), 7.45 (s, 1H), 7.23 (s, 1H), 3.66-3.72 (m, 1H), 3.48-3.53 (s, 1H), 2.34-2.46 (m, 1H), 2.18 (s, 3H), 1.96-2.10 (m, 3H), 1.46, 1.25 (s, 9H, rotamers, 1:2 ratio). LCMS: Anal. Calcd. for C29H32N6O3: 512; found: 513, 282 (M+H)+.

Provenance & Evidence