Diisopropylamine → HCID 59525951, compound

Temperature

-78 °C

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.

1. additionwas added dropwise
2. stirringAfter stirring for 1 hour at −78° C.
3. stirringstirring
4. waitcontinued for 30 minutes
5. extractionthe products extracted into EtOAc (2×)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification of the residue by flash column chromatography on silica gel (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc)

ORD record

ord-097797234ed54576924140c8f0f573a6

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2