Triethylamine → HCID 86728176, compound

Participants

Reaction Steps

To a stirred solution of triphenylphosphine (262 mg, 1.00 mmol) and 4-fluoroaniline (111 mg, 1.00 mmol) in CH2Cl2 (5 mL) was added dimethyl but-2-ynedioate (142 mg, 1.00 mmol) dropwise. The reaction mixture turned brown and was stirred for 1 h before triethylamine (139 μL, 1.00 mmol) and ethyl 2-chloro-2-oxoacetate (150 mg, 1.10 mmol) were added. The reaction mixture was stirred at rt for 14 h, concentrated and the residue was purified by ISCO, eluting with Hex/EtOAc (0-20% B over 15 min) to Intermediate 12 (180 mg, 0.530 mmol, 53.0% yield) as a white solid. HPLC/MS (Method L) RT=1.75 min, [M+H]+ 337.9.

Provenance & Evidence