Potassium Phosphate, Tribasic → 5-Cyclopropylnicotinonitrile

HRID 931137Notes

Reaction equation

HRID 931137 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1>[CH:10]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:7]=2)[C:8]#[N:9])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 7367935-BromonicotinonitrileHCID 2760897Cyclopropylboronic acid

Product 1

HCID 574196235-CyclopropylnicotinonitrileYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-5-cyanopyridine (1 g, 5.3 mmol) in tetrahydrofuran was added cyclopropyl boronic acid (0.5 g, 5.6 mmol) and potassium phosphate (1.08 g, 15.9 mmol). The resulting solution was degassed with nitrogen for 10 minutes and then palladium (II) acetate and S-phos were added. The reaction mixture was refluxed for 16 h. The reaction mixture was diluted with water, extracted with ethyl acetate and concentrated under reduced pressure. The crude material was purified via column chromatography to afford 5-cyclopropylnicotinonitrile (0.45 g, 58%). MS (ES+) (M+H) 145.1774.

Workup

  1. customThe resulting solution was degassed with nitrogen for 10 minutes
  2. additionpalladium (II) acetate and S-phos were added
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. additionThe reaction mixture was diluted with water
  5. extractionextracted with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography

Sources & evidence

ORD record
ord-fb23e4a5782d4d198fae2eb89dc570e7
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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