Cesium fluoride → HCID 86613182, compound

Participants

Reaction Conditions

Reaction Steps

Add cesium fluoride (0.221 g, 1.45 mmol) and dichloro[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.024 g, 0.029 mmol) to a mixture of propane-2-sulfonic acid [2-(4-bromo-phenyl)-2H-pyrazol-3-yl]-amide (0.100 g, 0.290 mmol) and 2-cyanophenylboronic acid (0.043 g, 0.290 mmol) in anhydrous 1,2-dimethoxyethane (5.0 mL). Deoxygenate the mixture thrice, immerse into a pre-heated (85° C.) oil bath, and stir for 30h. Dilute the mixture with water and dichloromethane, filter through Celite®, and wash through with dichloromethane. Concentrate the mixture, re-dissolve in dichloromethane, adsorb onto silica gel, and subject to silica gel flash column chromatography (12 g column, eluting with a gradient of 0-10% methanol/dichloromethane for 40 min., followed by (20% 2.0M NH3 in methanol/dichloromethane) to yield the title product as a light brown solid (0.036 g, 34%): mass spectrum (m/e): 367.0 (M+1), 365.0 (M−1).

Provenance & Evidence