Cesium carbonate → [5-(6-Methoxy-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)methanone (0.1 g, 0.30 mmol) was combined with 2-methoxypyridine-5-boronic acid (0.045 g, 0.3 mmol), caesium carbonate (0.142 g, 0.44 mmol), and palladium tetrakis(triphenylphosphine) (0.031 g, 0.03 mmol) in DME (6 mL), IMS (2 mL) and water (13 mL). The reaction mixture was heated by microwave irradiation to 140° C. for 20 minutes. The solution was partitioned between ethyl acetate and water and the phases separated then the organic phase was dried and evaporated to afford the title compound as a gum. The compound was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were evaporated to give the title compound as an oil (0.077 g). LCMS m/z 357.25 [M+H]+ R.T.=12.46 min (Analytical Method 2).

Provenance & Evidence