Isobutylamine → HCID 63589320, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-chloro-6-methoxypyridine (357 μL, 3 mmol), isobutylamine (596 μL, 6.00 mmol) and Caddick's Catalyst (prepared according to the literature reference Org. Biomol. Chem. 2008, 6, 2820) (35.3 mg, 0.060 mmol) under nitrogen, was added lithium hexamethyldisilazide in tetrahydrofuran (THF) (1 M, 3.750 mL, 3.75 mmol). This was warmed to 70° C. and stirred overnight, then cooled for analysis. The reaction was then further heated by microwaves to 150° C. for 30 minutes. After cooling, purification was attempted by flash silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient), but this failed to provide adequate separation. Purification was then repeated by flash silica (Si) chromatography (0-65% dichloromethane-cyclohexane gradient) to isolate the title compound (37.8 mg). LCMS (2 min, formic) Rt 0.75 min, m/z (ES+) 181 (M+H).

Provenance & Evidence