1-Chloroethyl chloroformate → HCID 22028200, compound

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Reaction Steps

A stirred solution under nitrogen of N-(2-{3-[(3-chlorophenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-1-yl}ethyl)-N,N-dimethylamine (0.540 g, 1.49 mmol) in 1,2-dichloroethane is treated with 1-chloroethyl chloroformate (0.40 mL, 3.7 mmol), heated at reflux temperature for 2 h cooled, and concentrated in vacuo. The resultant residue is treated with ethanol, heated at reflux temperature for 2 h and concentrated in vacuo. This resultant residue is chromatographed using 2:98 concentrated NH4OH:ethanol as eluent to afford the free amine of the title product as a semi-solid (311 mg, 60%). The free amine is dissolved in ethanol, treated with 4M HCl in dioxane and filtered. The filtercake is dried to give the title product as a pale yellow solid, 274 mg (48% yield), mp 263-265° C. (dec.), identified by mass spectral and HNMR analyses.

Provenance & Evidence