Dimethylformamide → HCID 178522941, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno[2,3-b]pyridine-5-carboxamide (2.00 g) from Example No. 2 in DMF (45 mL) are added triethylamine (1.25 mL), morpholine (15.7 mL), Pd(OAc)2(0.101 g), and dppp (0.186 g). The reaction mixture is degassed by bubbling N2 through the solution for 15 minutes. Carbon monoxide is then bubbled through the solution, and the reaction mixture is heated to 70° C. and stirred for 18 h. The reaction mixture is allowed to cool to room temperature and water (25 mL) and 2 N HCl (75 mL) are added. The resulting green solid is filtered off and the filtrate is extracted with CH2Cl2 (4×100 mL). The combined organic layers are dried with MgSO4, filtered, and concentrated in vacuo. The resulting orange oil is purified by column chromatography (CH2Cl2; CH2Cl2/methanol, 98/2). The resulting pale yellow solid is recrystallized from acetonitrile to yield 0.648 g (33%) of the title compound as an off-white solid.

Provenance & Evidence