Tetrahydrofuran → Ammonium hydroxide methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,4-dichloro-3-methyl-1,8-naphthyridine (210 mg, 0.986 mmol) in toluene (5 mL) was added dichloro 1,1′-bis(diphenylphosphino)-ferrocene palladium (II) (161 mg, 0.197 mmol), cyclopropylzinc bromide solution 0.5 m in THF (3.94 mL, 1.971 mmol). The reaction was heated at 100° C. for 2 h. After this time the reaction was cooled to rt and partitioned between EtOAc (60 mL) and water (20 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (DCM/DCM:—MeOH:NH4OH (9:1:0.4), 1:0 to 7:3 as eluent) gave 4-chloro-2-cyclopropyl-3-methyl-1,8-naphthyridine. Mass Spectrum (ESI) m/e=219.2.

Provenance & Evidence