Diisobutylaluminum hydride → HCID 59278372, compound

To a chilled (−78° C.) solution of 2-bromo-6-methyl-isonicotinic acid methyl ester (1.90 g, 8.26 mmol) in CH2Cl2 (200 mL) was added a 1 M solution of DIBAH (24.8 mL, 24.8 mmol) in CH2Cl2. The mixture was allowed to warm to room temperature. After 12 hours, the reaction was quenched with saturated aqueous sodium bicarbonate (100 mL). After 5 hours, phases were separated and the aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in heptane to afford (2-bromo-6-methyl-pyridin-4-yl)-methanol as white solid. MS m/z 202.45 (M+), 204.44 (M+2).

1. customthe reaction was quenched with saturated aqueous sodium bicarbonate (100 mL)
2. waitAfter 5 hours
3. customphases were separated
4. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 mL)
5. washThe combined organic layers were washed with brine (100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting residue was purified by silica gel chromatography
10. washeluting with a gradient of 0-100% ethyl acetate in heptane

ORD record

ord-0e5d93333e9046a3bd205f12fb1b4156

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338610B2