Acetic Acid → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide (45 mg, 0.13 mmol), 4-methoxy benzaldehyde (16 uL, 0.13 mmol), and glacial acetic acid (8 uL, 0.13 mmol) in methanol (1 mL) was added sodium triacetoxy borohydride (84 mg, 0.4 mmol) portionwise. The solution was stirred at 50° C. for 18 h. The solution was absorbed onto Celite and purified by ISCO Companion (silica 0-10% methanol, methylene chloride, 1% ammonium hydroxide) to afford 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide (56 mg, 75%) LCMS (ESI) 422 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 10.26 (1H, br. s.) 7.98-8.07 (2H, m) 7.77 (1H, d, J=5.47 Hz) 7.46 (1H, d, J=5.47 Hz) 7.30 (1H, d, J=3.32 Hz) 7.19 (2H, d, J=8.59 Hz) 6.76-6.84 (2H, m) 6.43 (1H, d, J=3.51 Hz) 3.69 (3H, s) 3.60 (2H, s) 3.33 (2H, q, J=6.25 Hz) 2.61 (2H, t, J=6.64 Hz)

Provenance & Evidence