Cesium carbonate → N-(4-bromobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

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Reaction Steps

The title compound was synthesized from 2-(4-chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol (302 mg, 1.0 mmol), cesium carbonate (652 mg, 2.0 mmol), and 1-bromo-4-(bromomethyl)benzene (300 mg, 1.2 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 2) to give N-(4-bromobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (341 mg, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 7.65-7.72 (2H, m), 7.40-7.46 (2H, m), 7.37 (2H, d, J=8.56 Hz), 7.18 (2H, d, J=8.56 Hz), 4.68 (2H, dd, J=38.27, 17.12 Hz), 3.97 (1H, t, J=7.30 Hz), 3.77 (1H, s), 1.94 (1H, hr. s.), 1.79-1.88 (3H, m), 1.36-1.62 (3H, m), 1.00-1.12 (2H, m). LC/MS R.T.=2.33 min; [M+H]+=470.03. HRMS [M+H]+ calc'd 470.0192, found 470.0202.

Provenance & Evidence