Acetic Acid → methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Participants

Reaction Steps

Methyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate (500 mg, 2.84 mmol) and hexamethylenetetramine (796 mg, 5.68 mmol) were combined in water (8 mL) and glacial acetic acid (16 mL) and heated at 100° C. overnight then cooled to room temperature. The reaction mixture was extracted with ethyl acetate and the organics were dried over MgSO4 and concentrated in vacuo to give a residue. Purification of the residue by silica gel chromatography (50% EtOAc/Hexanes) gave the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.07 (s, 1H), 8.57 (s, 1H), 8.48 (d, 1H, J=4.8 Hz), 7.48 (d, 1H, J=4.8 Hz), 5.74 (d, 1H, J=6.8 Hz), 3.91 (s, 3H), 2.78 (s, 3H). [M+H] found 205.

Provenance & Evidence