3-Bromopyridine → 3-Cyclopentylpyridine

HRID 2212078Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:8]1([Mg]Cl)[CH2:12][CH2:11][CH2:10][CH2:9]1>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl>[CH:8]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: -5 °C

Procedure

3-Bromopyridine (3.9 ml, 40 mmol) and [1,2-bis(diphenylphosphino)ethane]dichloronickel(II) (160 mg, 0.3 mmol) were dissolved in dry tetrahydrofuran (25 ml) and cooled to −5° C. Cyclopentylmagnesium chloride (2.0M in diethyl ether, 20 ml, 40 mmol) was added dropwise over 5–10 minutes and the reaction was allowed to warm slowly to room temperature. Further cyclopentylmagnesium chloride (2.0M in diethyl ether, 5 ml, 10 mmol) was added. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20–35% ethyl acetate/i-hexane, to give the title compound (1.74 g, 30%).

Workup

temperatureto warm slowly to room temperature
customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution
customThe mixture was partitioned between water and ethyl acetate
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica
washeluting with 20–35% ethyl acetate/i-hexane

Sources & evidence

ORD record: ord-27dc71682f4e4c5c9ea1b348d408e5df
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101892B2

Reaction notes

Loading…