1-Bromo-2-methylpropane → HCID 59214340, compound

Participants

Reaction Steps

To a solution of methyl 2-hydroxy-4-pyridinecarboxylate (D26; 1.02 g, 6.66 mmol) in N,N-dimethylformamide (20 ml) was added sodium hydride (60%; 0.293 g, 7.33 mmol). The resulting solution was stirred at room temperature for 15 mins. 1-Bromo-2-methylpropane (0.87 ml, 7.99 mmol) was then added and the mixture was stirred at 80° C. for 2 hrs. The reaction was quenched with methanol and the solvent was removed under vacuum. The residue was partitioned between ethyl acetate and water, the organic layer dried over magnesium sulphate and concentrated under vacuum. The crude material was purified by chromatography on silica, eluting with 50-80% ethyl acetate in cyclohexane gave the title compound as a light blue solid (450 mg). MS: m/z 210 [MH+]. O-alkylated material was also isolated.

Provenance & Evidence