Triphenylphosphine → HCID 68765039, compound

Participants

Reaction Steps

Under a nitrogen atmosphere 100 mg of methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate, 57.2 mg of (1S)-1-(2-chlorophenyl)ethanol and 95.7 mg triphenylphosphine are dissolved in 1 ml anhydrous THF. To this mixture a solution of 80.9 mg diisopropyl azodicarboxylate in 0.5 ml anhydrous THF is added dropwise and the mixture is stirred for 14 h at room temperature. The solvent is evaporated under vacuum. After extraction with ethyl acetate and a saturated solution of sodium chloride, the organic phase is dried over MgSO4. The solvent is removed under vacuum and the remaining residue is dissolved in 2 ml dichloromethane and filtered through a short plug of silica gel (eluent: ethyl acetate). After evaporation of the solvent, the remaining residue and 20 ml of a saturated solution of ammonia in methanol are stirred in a microwave vial at 125° C. for 8 h in the microwave cavity. Subsequently the solvent is removed under vacuum. The remaining residue is dissolved in 2 ml dichloromethane and is purified by flash chromatography (eluent: ethyl acetate, followed by ethyl acetate/methanol 95/5 (v/v)) to yield the title compound.

Provenance & Evidence