Sodium Carbonate → 6,7-Dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

HRID 1626125Notes

Reaction equation

Cl[C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][N:18]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC>[N:4]1[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=[C:2]([C:17]#[N:18])[CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-chloro-6,7-dihydro-5H-[1]pyrindine (7.1 g, 46.2 mmol), sodium carbonate (980 mg, 9.25 mmol), potassium hexacyanoferrate(II)trihydrates (7.81 g, 18.5 mmol), palladium(II) acetate (104 mg, 462 μmol) and butyldi-1-adamantylphosphine (497 mg, 1.39 mmol) was dissolved in N-methyl-2-pyrrolidinone (46.2 ml), the solution flushed with argon and heated to 160° C. for 16 hours. After cooling to 23° C., the mixture was poured into water, extracted with dichloromethane, the combined extracts dried over sodium sulphate and the solvent evaporated leaving a dark blue liquid. The crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 6,7-dihydro-5H-[1]pyrindine-3-carbonitrile as a white solid (4.82 g, 72% yield). MS (ISP): m/z=145.1 [M+H]+.

Workup

customthe solution flushed with argon
temperatureAfter cooling to 23° C.
additionthe mixture was poured into water
extractionextracted with dichloromethane
dry with materialthe combined extracts dried over sodium sulphate
customthe solvent evaporated
customleaving a dark blue liquid
customThe crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record: ord-b43cde48b4814ab19afd4dc2e3cfa27e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785436B2

Reaction notes

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