Triethylamine → 3-[5-(4-Chloro-phenyl)-pyridin-2-yl]-prop-2-yn-1-ol

Participants

Reaction Conditions

Reaction Steps

Under an N2 atmosphere 1 mL (7.22 mmol) triethylamine, 23 mg (0.1 mmol) Pd(OAc)2 and 57.5 mg (0.19 mmol) biphenyl-2-yl-di-tert-butyl-phosphane are added to a solution of 500 mg (2.36 mmol) 3-(5-bromo-pyridin-2-yl)-prop-2-yn-1-ol and 600 mg (3.72 mmol) 4-chlorophenyl-boric acid in 10 mL DMF and 2.5 mL water and the reaction mixture is stirred for 8 h at 60° C. Then 400 mg (2.48 mmol) 4-chlorophenyl-boric acid are added and the mixture is stirred for a further 19 h at 60° C. The mixture is evaporated down i. vac., the residue is combined with 10 mL water and 10 mL EtOAc, the aqueous phase is saturated with NaCl, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc3 2:1).

Provenance & Evidence