Ethanol → HCID 178469171, compound

Participants

Reaction Steps

To a solution of (E)-diethyl 2-(1-((1-(2,3-difluorobenzyl)pyrrolidin-2-ylidene)amino)ethylidene)malonate (36.3 g, 69.9 mmol) in N,N-dimethylformamide (DMF) (140 mL) was added sodium ethoxide (78 mL, 210 mmol) (21% wt./EtOH) and the mixture was placed in a pre-heated oil bath at 100° C. and stirred for 1 h. The mixture was cooled to ambient temperature and then poured slowly into cold 1 N HCl/water (−150 mL) and then more 1N HCl/water was added to pH 8-9. After stirring at 0° C. for 30 min The solid was filtered, washed with water and dried in vacuo for 18 h to provide ethyl 1-(2,3-difluorobenzyl)-4-hydroxy-6-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (10 g, 27.3 mmol, 39.0% yield) as a light tan solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42 (t, J=7.12 Hz, 3 H), 2.66 (s, 3 H), 2.95 (t, J=8.68 Hz, 2 H), 3.53 (t, J=8.78 Hz, 2 H), 4.39 (q, J=7.02 Hz, 2 H), 4.72 (s, 2 H), 6.90-7.20 (m, 3 H), 11.94 (s, 1 H); LCMS (m/z) ES+=349 (M+1).

Provenance & Evidence