2,6-Dibromopyridine → 3-[(6-Bromopyridin-2-yl)(hydroxy)methyl]benzonitrile

Temperature

-78 °C

To a mixture of 2,6-dibromopyridine (6 g, 25.33 mmol) in anhydrous THF (150 mL) under N2 @−78° C. was added n-BuLi (10.13 mL, 2.5M) dropwise. The mixture was stirred @ −78° C. for 15 min and 3-cyanobenzaldehyde (3.32 g, 25.33 mmol) in anhydrous THF (10 mL, rinsed with 5 mL) was added. The mixture was stirred for 20 min @ −78° C. then warmed to 0° C. and stirred for 1 hr. The mixture was quenched with saturated aqueous NH4Cl, and the resulting mixture was extracted 3× with EtOAc. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (15-30% EtOAc in Hexanes) to give 3-[(6-bromopyridin-2-yl)(hydroxy)methyl]benzonitrile. LRMS m/z (M+H) Calcd.: 289.0, found 289.1.

1. stirringThe mixture was stirred for 20 min @ −78° C.
2. temperaturethen warmed to 0° C.
3. stirringstirred for 1 hr
4. customThe mixture was quenched with saturated aqueous NH4Cl
5. extractionthe resulting mixture was extracted 3× with EtOAc
6. dry with materialThe combined organics were dried (anhd. Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography (15-30% EtOAc in Hexanes)

ORD record

ord-d6e8acb0bc5c473dae39d3b24ee6002e

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569589B2