Diisopropylamine → HCID 58952079, compound

Participants

Reaction Steps

A mixture of (3,4-difluoro-benzyl)-prop-2-ynyl-carbamic acid tert-butyl ester (3.2 g, 11.4 mmol), 4-chloroiodobenzene (4.1 g, 17.2 mmol, 1.5 eq.), Pd(PPh3)2Cl2 (0.4 g. 0.57 mmol, 5 mol %), iPr2NH (4 mL, 28.5 mmol, 2.5 eq.) and CuI (0.435 g, 2.3 mmol, 0.2 eq.) in 100 mL dichloromethane was stirred overnight at room temperature. The solution was diluted with 300 mL ether and filtered through a CELITE pad to remove the insoluble components. The filtrate washed with 2×100 mL 1N HCl, 100 mL brine, dried over MgSO4, filtered, concentrated and chromatographed with 6% ethyl acetate in hexanes to provide 2.6 g of [3-(4-chloro-phenyl)-prop-2-ynyl]-(3,4-difluoro-benzyl)-carbamic acid tert-butyl ester.

Provenance & Evidence