Potassium Phosphate, Tribasic → 2-Cyclopropylpyridine-3-carbonitrile

HRID 2218311Notes

Reaction equation

HRID 2218311 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH:10]1([C:2]2[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:11]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 810792-ChloronicotinonitrileHCID 2760897Cyclopropylboronic acid

Product 1

HCID 574409062-Cyclopropylpyridine-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Chloro-3-cyano-pyridine (9.69 g, 70.0 mmol), cyclopropylboronic acid (7.21 g, 84.0 mmol), Pd(OAc)2 (875 mg, 3.50 mmol), tricyclohexylphosphine (1.96 g, 7.00 mmol), and K3PO4 (44.5 g, 210 mmol) were suspended in toluene (280 ml) and H2O (14 ml) and heated at 100° C. for 5 h. The reaction mixture was dried over MgSO4 and the mixture was filtered through Celite, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 7/3) to obtain the intended compound as a pale yellow solid.

Workup

  1. dry with materialThe reaction mixture was dried over MgSO4
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 7/3)

Sources & evidence

ORD record
ord-9e0f59f72bb04bd4a0f20d1a053284c4
Source dataset
uspto-grants-2008_08
Patent number
US07410976B2

Reaction notes

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