Dimethylformamide → 5-(1,3-Dioxolan-2-yl)pyridine-2-carbonitrile

HRID 1186404Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1.[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1)#[N:14]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Bromo-5-(1,3-dioxolan-2-yl)pyridine (895 mg, 3.89 mmol), zinc cyanide (1.14 g, 5.83 mmol) and tetrakis(triphenylphosphine)palladium (899 mg, 0.778 mmol) were dissolved in N,N-dimethylformaldehyde (30 ml) and the mixture was heated to reflux at 80° C. under a nitrogen atmosphere for 12 hours. The reaction mixture was concentrated, water was added thereto, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=7/3) to give 2-cyano-5-(1,3-dioxolan-2-yl)pyridine (506 mg, yield: 74%).

Workup

temperaturethe mixture was heated
concentrationThe reaction mixture was concentrated
additionwater was added
extractionextraction with ethyl acetate
washby washing with brine
dry with materialdrying over anhydrous sodium sulfate
customThe solvent was evaporated off under reduced pressure
customthe residue was purified by column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record: ord-a5ba6289b800431695f6b82e29b79c1c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673908B2

Reaction notes

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