Cesium carbonate → HCID 89922979, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromo-4-chlorobenzonitrile (160 mg, 0.542 mmol), (3R,4R)-methyl 4-amino-3-hydroxypiperidine-1-carboxylate (88 mg, 0.505 mmol), Pd2(dba)3 (69.4 mg, 0.076 mmol), BINAP (47.2 mg, 0.076 mmol), and Cs2CO3 (494 mg, 1.516 mmol) in a dry microwave vial was flushed with nitrogen. Toluene (3.7 mL) was added and the vial was sealed and heated at 105° C. for 4 hours. The reaction was partitioned between EtOAc and water. The organic phase was washed with brine and dried with sodium sulfate. Removal of the solvent followed by silica gel chromatography eluting with hexane containing 20% to 50% EtOAc afforded (3R,4R)-methyl 4-((3-bromo-2-chloro-5-cyanophenyl)amino)-3-hydroxypiperidine-1-carboxylate (20 mg).

Provenance & Evidence