Cesium carbonate → Ethyl 4-amino-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate (Description 15) (1.52 g, 3.61 mmol), tert-butyl carbamate (0.845 g, 7.22 mmol), Pd2(dba)3 (0.066 g, 0.072 mmol), xantphos (0.084 g, 0.144 mmol) and Cs2CO3 (3.53 g, 10.82 mmol) in 1,4-dioxane (25 mL) was heated at 110° C. for ca. 6 h. After cooling to RT, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by chromatography, eluting with a gradient of 30-60% ethyl acetate in cyclohexane, to give the title compound (1.54 g). LCMS (A) m/z: 458 [M+1]+, Rt 1.44 min (acidic).

Provenance & Evidence