Cesium carbonate → HCID 89813930, compound

Participants

Reaction Conditions

Reaction Steps

A pressure vessel was charged with 4-bromo-5,6,7,8-tetrahydro-1,7-naphthyridine hydrobromide (331 mg, 1.126 mmol), 2-methoxy-4-(trifluoromethyl)phenylboronic acid (488 mg, 2.219 mmol), cesium carbonate, 99.9% (metal basis) (0.275 mL, 3.44 mmol), and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (ii) dichloromethane adduct (86 mg, 0.105 mmol). Dioxane (2 mL) and water (0.4 mL) were added, and argon was streamed into the vessel for about 20 seconds. The mixture was stirred in a 70° C. oil bath for two hours, then diluted with CH2Cl2 and washed with H2O. The layers were separated and the water layer was extracted with another portion of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by column chromatography (Combiflash, 40 gram Redisep gold column), eluting with 0-100% (3:1 EtoAc/EtOH with 2% NH4OH in heptane) to obtain 4-(2-methoxy-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-1,7-naphthyridine (232 mg, 0.753 mmol, 66.8% yield) as a brown viscous oil. [M+H]+=309.0.

Provenance & Evidence