Cornforth reagent → 2-chloro-N-{1-[2-(methylcarbamoyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

Participants

Reaction Steps

Pyridinium dichromate (329 mg, 0.88 mmol) was added to 2-chloro-N-[1-(3-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 43; 100 mg, 0.248 mmol) in DMF (3 mL) and the reaction was stirred for 24 hours. The reaction was diluted with EtOAC (20 mL) and filtered through celite. The filtrate was washed with 1M HCl (aq.) and the organic layer was dried (MgSO4), filtered and evaporated to afford the crude acid which was used without purification. Standard amide bond formation analogous to Method 3 except using methylamine (2.0 M in THF) as amine gave the title compound (65 mg, 61% over 2 steps) as a white solid.

Provenance & Evidence