Bromide ion → HCID 57666057, compound

Participants

Reaction Conditions

Reaction Steps

4-Methyl-2-[4′-trifluoromethyl-5-(6-trifluoromethyl-piperidin-2-yl)-biphenyl-3-yl]-pentanoic acid ethyl ester, compound 7b (47 mg, 0.092 mmol), 4-Methoxybenzyl bromide (66 μl, 0.46 mmol), DIEA (160 μl, 0.919), and tetrabutylammonium iodide (TBAI)(36 mg, 0.096 mmol) were combined and heated to 80° C. After overnight, no product was formed. Cesium carbonate (30 mg, 0.46 mmol) was added and after 5.5 hours ˜30% product was obtained. Additional Cesium carbonate (30 mg), bromide (66 ml) and TBAI were added and the reaction continued 72 hours. Little change in product formation. Reaction was purified directly by silica gel chromatography to give 21.3 mg, 36% as a clear oil. (M+H) 635.38, Found 636.4.

Provenance & Evidence