Dimedone → HCID 178470356, compound

Participants

Reaction Conditions

Reaction Steps

387 μmol of 3-amino-2-ethoxycarbonylpyrrole hydrochloride, 387 μmol of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from example 108, step 1), 387 μmol of dimedone and 202 μL of N,N-diisopropylethylamine in 1.5 mL of ethanol are poured into a flask suitable for microwave irradiation (Personal Chemistry model Emrys Optimizer instrument). The flask is locked then irradiation is performed at 100° C. during 700 seconds. After cooling down to 20° C., the reaction mixture is concentrated under reduced pressure. The residue is purified on silica gel (Analogix model Intelliflash 280 instrument, SiO2 40 g; Eluent EtOAc/cyclohexane; from 30/70 to 75/25. (v/v), rate: 25 mL/min, during 70 minutes). The fractions containing the expected compound are combined and concentrated under reduced pressure. The remaining oil is solubilized in 0.5 mL of dichloromethane (DCM) then crystallized by addition of small amounts of diisopropyloxide. 62 mg of expected compound are collected as a solid.

Provenance & Evidence