Methanol → HCID 178496975, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno[2,3-b]pyridine-5-carboxamide (2.61 g) from Example No. 2 in DMF (33 mL) are added triethylamine (1.6 mL), methanol (9.5 mL), Pd(OAc)2(0.132 g), and dppp (0.242 g). Carbon monoxide is bubbled through the solution, and the reaction is heated to 70° C. The reaction is stirred at 70° C. for 18 h. The reaction mixture is cooled to rt, and water (25 mL) and 2 N HCl (25 mL) are added. The resulting precipitate is filtered off and purified by column chromatography (CH2Cl2; CH2Cl2/methanol, 99/1; 98/2). A mixture of starting material and desired product is isolated as a yellow solid. This material is re-subjected to the reaction conditions above. The reaction is stirred at 70° C. for 18 h. The reaction is cooled to rt and water (25 mL) and 2 N HCl (25 mL) are added. The resulting orange solid is filtered off and purified by column chromatography (CH2Cl2; CH2Cl2/methanol, 99/1; 98/2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield a pale yellow solid which is recrystallized from methanol to yield 1.337 g (60%) of the title compound as a pale yellow, crystalline solid.

Provenance & Evidence