2-(Di-tert-butylphosphino)biphenyl → Methyl-[1-(2-thiophen-3-yl-pyridin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-2-thiophen-3-yl-pyridine (50 mg, 0.4 mmol) in toluene (1 mL) was added Pd(OAc)2 (2.3 mg, 0.01 mmol), 2-(di-t-butyl-phosphino)biphenyl (6.0 mg, 0.02 mmol), methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (60 mg, 0.45 mmol), and NaOtBu (75 mg, 0.8 mmol). The resulting mixture was stirred at 90° C. for 16 h, then was cooled, poured into water, and extracted with EtOAc. The organic layer was dried and concentrated, and the resulting residue was purified by preparative TLC (hexanes/EtOAc) to yield methyl-[1-(2-thiophen-3-yl-pyridin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a white solid (60 mg, 42%).

Provenance & Evidence