Sodium hydride → HCID 54691510, compound

Participants

Reaction Steps

To a suspension of either NaH (60% suspension in mineral oil, pre washed with hexanes, 0.25 g, 6.2 mmol) held at room temperature or Lithium diisopropylamide (LDA, 2M solution in THF, 11.3 mmol, 5.6 mL) held at −78° C. in THF (30 mL) was added a solution of 2-(2-cyano-acetylamino)-4-(3,5-dimethyl-phenyl)-thiophene-3-carboxylic acid ethyl ester (0.968 g, 2.83 mmol) in THF (15 mL) dropwise via syringe over 10 minutes. The mixture was stirred at room temperature for 5 hours (or in the case of LDA, allowed to warm to room temperature over 16 hours), cooled to 0° C. and then quenched by dropwise addition of MeOH (5 mL) followed by 1N HCl to adjust the pH <3. The resultant slurry was filtered and the solid was washed with water (4×4 mL), ether (3×4 mL) and (Na2SO4), filtered and concentrated under reduced pressure to provide the target compound. The filtrate was concentrated and purified on a RP-HPLC system to provide additional compound. MS (ESI) m/e 295 (M−H)+; 1H NMR (300 MHz, MeOH-d4): δ ppm 12.53 (br s, 1H), 7.04 (s, 2H), 6.99 (s, 1H), 6.90 (s, 1H), 2.32 (s, 6H).

Provenance & Evidence