Sodium Bicarbonate → HCID 59161227, compound

Participants

Reaction Steps

Heat (R)-N-(6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Example 127) (4.00 g, 10.3 mmol) with thioacetamide (1.54 g, 20.5 mmol) at reflux in 4N HCl in dioxane (100 mL) for 16 h. Cool the reaction, pour onto water, and neutralize with NaHCO3. Extract with EtOAc and evaporate to 4.2 g of a red foam. Purify using silica gel chromatography, eluting with 25-100% EtOAc/hexanes gradient to give 2.6 g (60%) of a yellow solid. MS (ES): m/z 424 (M+1); HPLC: Rt=1.90 min (95%).

Provenance & Evidence