Diisobutylaluminum hydride → HCID 54678080, compound

Participants

Reaction Steps

1M DIBAL-H (10 mL, 10 mmol) was slowly added to a solution of methyl 4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)benzoate (0.3 g, 0.832 mmol) in anhydrous THF (80 mL) held at −78° C. The solution was then allowed to warm to rt and stirred overnight. The reaction was quenched with MeOH (2 mL) and 1N HCl (5 mL), filtered through silica gel, concentrated and purified on a RP-HPLC system. MS (ESI) m/e 330.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 7.35 (d, J=8.28, 2H), 7.29 (d, J=7.98, 2H), 4.60 (br s, 1H), 4.55 (s, 2H).

Provenance & Evidence