Tetrahydrofuran → Methyl 3-amino-6-(thiazol-2-yl)picolinate

Participants

Reaction Steps

A solution of methyl 3-amino-6-bromopicolinate (1.0 equiv.), 2-thiazolylzinc bromide 0.5 M solution in THF (3.0 equiv.), and Pd(dppf)Cl2-DCM (0.05 equiv.) was stirred at 80° C. for 1.5 hours. The reaction was filtered and washed with EtOAc. The organic was washed with H2O (100 mL), and further washed with NaCl(sat.) (50 mL), dried over MgSO4, and the volatiles were removed in vacuo. The product was crystallized with hexane/EtOAc (1:1) to yield methyl 3-amino-6-(thiazol-2-yl)picolinate (51%). LCMS (m/z): 236.1 (MH+); LC Rt=2.3 min.

Provenance & Evidence