Diisopropylamine → HCID 59525951, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (0.73 mL, 5.09 mmol) was taken up in THF (10 mL) and cooled to −78° C. n-BuLi (2.04 mL, 5.09 mmol) was added dropwise and the resulting mixture stirred at −78° C. for 90 minutes. The resulting LDA solution was transferred by cannula to a solution of 2-bromo-6-methylpyridine (500 mg, 2.91 mmol) in THF (20 mL) at −78° C. After stirring for 1 hour at −78° C., a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (640 mg, 5.81 mmol) in THF (3 mL) was added and stirring continued for 30 minutes. Saturated NH4Cl was added and the products extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc) gave the title compound as a white solid.

Provenance & Evidence