Dichloromethane → HCID 69267558, compound

Participants

Reaction Steps

(1R,2R)-2-(2-Bromophenyl)-N-(1-cyanocyclopropyl)-5,5-difluorocyclohexanecarboxamide (518 mg, 1.35 mmol), 4-(methylthio) benzeneboronic acid (285 mg, 1.70 mmol), PdCl2(dppf).CH2Cl2 (61 mg, 0.075 mmol) and 2.0 M Na2CO3 aqueous solution (1.02 mL, 2.04 mmol) were heated at 85° C. in N,N-dimethylformamide (4.0 mL) under a nitrogen atmosphere. After 17 hours at this temperature, the reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water and the layers separated. The aqueous phase was extracted with additional ethyl acetate and the combined organics were washed with brine, and dried (Na2SO4). Concentration in vacuo and chromatography of the residue on silica eluting with 30/70 EtOAc/hexanes gave the title compound as a faint-yellow foam, [αD=−41° (c=0.95, CHCl3), MS (−ESI): 425.3 [M−H]−.

Provenance & Evidence