2-Bromoethanol → N-[(4-chlorophenyl)methyl]-7-(2-hydroxyethyl)-2-(3-hydroxypropyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(3-hydroxypropyl)-thieno-[2,3-b]pyridine-5-carboxamide (Example No. 8) (0.330 g) in DMF (5 mL) are added K2CO3 (0.363 g) and 2-bromoethanol (0.19 mL). The reaction is heated to 100° C. and stirred for 18 h. An additional 0.19 mL of 2-bromoethanol is added and stirring is continued for 18 h. An additional 0.19 mL of 2-bromoethanol and 0.363 g of K2CO3 is added. After 5 h, 35 mg of NaH (60% oil dispersion) is added. The reaction is stirred for 1 h. The reaction mixture is cooled to rt and concentrated in vacuo. The residue is suspended in CH2Cl2 and H2O. The resulting off-white precipitate is filtered off and purified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.145 g (39%) of the title compound as a white solid.

Provenance & Evidence