3-Bromopyridine → HCID 68899458, compound

3-Bromopyridine (1 g, 6.3 mmol) was added in a dropwise fashion to a stirred, −78° C. solution of lithium diisopropylamide (1.8 M commercial solution; 3.7 mL, 6.7 mmol) in THF (16 mL). After 10 minutes, cyclobutanone (0.52 mL, 7.0 mmol) was added dropwise and stirring was continued for 1 hour at −78° C., prior to warming to ambient temperature. After stirring for a further 30 minutes, the reaction was quenched by addition of saturated aqueous NH4Cl (10 mL) and the mixture partitioned between EtOAc (100 mL) and water (100 mL). The organic fraction was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting crude product was purified by flash column chromatography on silica (eluent 50% EOAc/isohexane) to afford 1-(3-bromopyridin-4-yl)cyclobutanol as an off-white solid (412 mg). m/z (ES+) 228/230 [MH+].

1. waitwas continued for 1 hour at −78° C.
2. stirringAfter stirring for a further 30 minutes
3. customthe reaction was quenched by addition of saturated aqueous NH4Cl (10 mL)
4. customthe mixture partitioned between EtOAc (100 mL) and water (100 mL)
5. washThe organic fraction was washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting crude product was purified by flash column chromatography on silica (eluent 50% EOAc/isohexane)

ORD record

ord-4b564e529a464f3bb52e30f844814c32

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592456B2