Dichloromethane → Methyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanecarboxylate

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.55 mmol, 131 mg), K3PO4 (1.36 mmol, 290 mg), and PdCl2(dppf).CH2Cl2 (0.045 mmol, 37 mg) is added to a solution of 4-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-iodo-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester (0.45 mmol, 300 mg) in dioxane (3.8 mL). To this suspension is added distilled H2O (0.38 mL). The resulting solution is stirred at 90° C. under argon for 18 hours. The reaction mixture is concentrated in vacuo and then purified via silica gel chromatography (0% to 60% ethyl acetate in hexanes gradient) to yield the title compound (220 mg, 75% yield) as yellow oil. LC-MS: 646 [M+H].

Provenance & Evidence