Water → HCID 11782405, compound

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Reaction Steps

1-(Phenylsulfonyl)-1H-indole-4-carbaldehyde, Intermediate 5 (45.4 g, 0.159 mol) was dissolved in nitromethane (300 ml) and ammonium acetate (4.9 g, 0.064 mol, 0.4 eq.) was added. Mixture was heated at reflux for 4 hours and left overnight at ROOM TEMPERATURE Water (150 ml) was added, organic phase was separated. The aqueous phase was extracted with DCM (3×50 ml). Combined organic phase was washed with brine and dried on Na2SO4. The crude material (HPLC purity 85%) was passed through a silica column using DCM/EtOAc (8:1) as eluent. The product containing fractions were evaporated to a small volume when crystallization started. The yellow crystals were filtered, washed with petro/ether/EtOAc (2:1), and dried in vacuo. Yield: 33.1 g. MS m/z 329 [M+H]+.

Provenance & Evidence