Triethylamine → [1-(5-Methylsulfanyl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

In a Biotage microwave vial was placed [1-(5-iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (500 mg, 1.39 mmol), sodium thiomethoxide (292 mg, 4.17 mmol) and Xantphos (80 mg, 0.14 mmol). The vial was flushed with Ar. 1,4-Dioxane (7.5 ml) and Et3N (0.48 mL, 2.78 mmol) were added. Ar was bubbled through the reaction solution for 15 minutes. Pd2(dba)3 (65 mg, 0.07 mmol) was added and the reaction was thermally heated to 100° C. After 8 h, the reaction was transferred to a separatory funnel, diluted with saturated NaHCO3 and brine, and extracted with EtOAc (2×50 mL). The combined organic layers were dried, filtered and evaporated to give a black oil. Flash chromatography (10 g silica, 0-10% MeOH in DCM) yielded 300 mg of [1-(5-methylsulfanyl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester as a dark oil.

Provenance & Evidence