Cesium carbonate → HCID 68926468, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-6-bromo-5-fluoro-1-(1-(4-fluorophenyl)ethyl)-1H-benzo[d]imidazole (Method 44; 0.200 g, 0.59 mmol), 5-amino-3-cyclopropyl-1H-pyrazole-1-carboxylic acid tert-butyl ester (0.166 g, 0.741 mmol), Pd2 dba3 (0.011 g, 0.012 mmol), Xantphos (0.021 g, 0.036 mmol), and Cs2CO3 (0.483 g, 1.48 mmol) in toluene (5 ml) was heated at reflux for 18 hrs. To this was added 10 ml of EtOAc and saturated NH4Cl solution (10 ml). The organic layer was separated, washed with brine (10 ml), dried over Na2SO4, and concentrated under reduced pressure. The resulted residue was dissolved in the mixture of DCM:TFA (3:1 v/v, 4 ml), stirred at 25° C. for 2 hrs, concentrated, and treated carefully with saturated NaHCO3 solution (5 ml). The aqueous layer was extracted with DCM (10 ml), dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography (EtOAc) to give the title compound as a white solid (0.135 g, 60%). NMR (400 MHz) 11.71 (br, 1H), 8.30 (s, 1H), 8.04 (rb, 1H), 7.91 (s, 1H), 7.40 (d, J=12 Hz, 1H), 7.31 (m, 2H), 7.18 (m, 2H), 5.67 (m, 1H), 5.53 (s, 1H), 1.93 (br, 3H), 1.84 (m, 1H), 0.92 (m, 2H), 0.65 (m, 2H). MS: Calcd.: 379; Found: [M+H]+ 380.

Provenance & Evidence