Triethylamine → HCID 21833747, compound

Participants

Reaction Steps

2'-Methyl-4'-(1-methylimidazol-5-yl)biphenyl-4-carboxylic acid (D93, 300 mg, 1.0 mmol) was heated at reflux in thionyl (15 ml) for 1 hour, cooled and evaporated in vacuo. The residue was redissolved in dry THF (10 ml) and treated with 1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (D8, 250 mg, 1.0 mmol) and triethylamine (143 ul, 1.0 mmol) then stirred for 18 hours. The reaction mixture was evaporated in vacuo, partitioned between water and CHCl3 (3 times) and the organic extracts combined. The organics were dried over Na2SO4 and evaporated in vacuo to an orange gum. The gum was purified by flash silica gel chromatography (eluting with 3% MeOH/CHCl3) to yield the title compound as a pale yellow gum (200 mg, 38%) which was converted to the hydrochloride salt.

Provenance & Evidence