1,2-Dimethoxyethane → HCID 58629869, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (187 mg, 0.162 mmol) and Na2CO3 (1.29 g, 12.2 mmol) was treated with DME (20 mL) and stirred under nitrogen for 2 min. Water (10 mL), (1R)-1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethanol (1.0 g, 4.1 mmol) and (4-cyanophenyl)boronic acid (656 mg, 4.47 mmol) were added and the stirred reaction mixture heated at 80° C. for 17 h. The mixture was then allowed to cool to ambient temperature and the residue partitioned between saturated NH4Cl (100 mL) and EtOAc (100 mL). The aqueous phase was extracted with EtOAc (2×100 mL) and the combined organic extracts washed with brine (100 mL), dried (Na2SO4) and evaporated to give a yellow oil (1.43 g). Purification by Biotage™ chromatography (silica, 40 g cartridge) eluting with cyclohexane:EtOAc (4:1) afforded the title compound as a pale yellow oil (945 mg).

Provenance & Evidence