Potassium Phosphate, Tribasic → 5-Cyclopropylpicolinonitrile

HRID 657734Notes

Reaction equation

HRID 657734 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([CH:10]2[CH2:12][CH2:11]2)=[CH:7][N:6]=1)#[N:9]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 38339425-Chloro-2-cyanopyridine

Product 1

HCID 248646065-Cyclopropylpicolinonitrile

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-chloro-2-cyanopyridine (1.25 g, 9.02 mmol), cyclopropylboronic acid (1.00 g, 11.7 mmol), potassium phosphate (6.70 g, 31.6 mmol), tricyclohexylphosphine (380 mg, 1.4 mmol), toluene (200 mL), and water (2 mL) under argon was added palladium acetate (150 mg, 0.68 mmol). The mixture was heated at 100° C. overnight and then cooled to rt. The mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was washed with water, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (EtOAc/hexane: 0-50%) to yield a light yellow oil which becomes solid while standing at room temperature.

Workup

  1. temperaturecooled to rt
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter cake was washed with EtOAc
  4. washThe filtrate was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column (EtOAc/hexane: 0-50%)
  8. customto yield a light yellow oil which
  9. customwhile standing at room temperature

Sources & evidence

ORD record
ord-9c4e5a509cf54a96ba1aebc9ffe0fc63
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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