2-Chloronicotinonitrile → HCID 22180766, compound

HRID 1796105Notes

Reaction equation

HRID 1796105 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Sn](CCCC)(CCCC)CCCC)[N:3]=1.Cl[C:22]1[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][N:23]=1>C1COCC1.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>[Cl:1][C:2]1[N:3]=[C:4]([C:22]2[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 810792-ChloronicotinonitrileHCID 117844186-Chloro-2-(tributylstannyl)pyridine

Product 1

HCID 22180766HCID 22180766, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a degassed solution of 2-chloro-6-tributylstannylpyridine (prepared according to S. Choppin et al. in Org. Lett., 2000, 2, 803-5) (600 mg, 1.49 mmol) and 2-chloro-3-cyanopyridine (412 mg, 2.98 mmol) in THF was added tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) and the mixture heated at reflux for 96 hours. The solvent was removed under reduced pressure and the crude product chromatographed on silica, on a gradient of dichloromethane to 2% methanol in dichloromethane, to afford 6′-chloro-2,2′-bipyridinyl-3-carbonitrile as a white solid (231 mg): δH (400 MHz, d6-DMSO) 7.71-7.74 (2H, m), 8.11 (1H, t, J 7.8), 8.20-8.23 (1H, m), 8.48 (1H, dd, J 1.8, 8.0), 8.97 (1H, dd, J 1.8, 4.9); m/z (ES+) 216, 218 (M++H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 96 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product chromatographed on silica, on a gradient of dichloromethane to 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-07359306b52b4df2a972e52dc810fae4
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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