Water → HCID 86670208, compound

Participants

Reaction Steps

A 2.5M solution of n-buthyllithium (0.44 mL, 1.1 mmol) was added dropwise to a stirred solution of diisopropylamine (0.16 mL, 1.15 mmol) in THF (2 mL) at −78° C. The mixture was stirred for 15 minutes and 2-bromo-6-methylpyridine (0.11 mL, 1 mmol) was added dropwise. The mixture was stirred for 15 minutes and 1-bromo-2-methylpropane (0.21 mL, 2 mmol) was added dropwise. The mixture was stirred for 1 hour at this temperature and at room temperature for 60 hours. The mixture was treated with water and extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-bromo-6-(3-methyl-butyl)-pyridine (82 mg, 36% yield) as a colourless oil.

Provenance & Evidence