Tetrahydrofuran → 4-[(2-Butyl imidazo(1,2-a)pyridine 3-yl) methyl]benzonitrile

HRID 37212Notes

Reaction equation

HRID 37212 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[CH2:11][CH2:12][CH2:13][CH3:14].O1[CH2:19][CH2:18][CH2:17][CH2:16]1>[Pd].BrCC1C=CC(C#N)=CC=1.[Zn].O>[CH2:11]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:2]=1[CH2:16][C:17]1[CH:13]=[CH:12][C:11]([C:3]#[N:4])=[CH:19][CH:18]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 151299083-Bromo-2-butylimidazo[1,2-a]pyridine

Product 1

HCID 190324684-[(2-Butyl imidazo(1,2-a)pyridine 3-yl) methyl]benzonitrile

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 69459885HCID 69459885, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2 g of the product of Stage D, 100 ml of tetrahydrofuran and 1 -g of [tetra-bis(triphenylphosphine)] palladium was added to 35.9 ml of zinc 4-bromomethyl benzonitrile at ambient temperature and the mixture was refluxed for one hour. The mixture was allowed to return to ambient temperature, poured into water and extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried, filtered and brought to dryness to obtain after chromatography on silica (ethyl acetate), 1.1 g of the expected product.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. customto return to ambient temperature
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. filtrationfiltered

Sources & evidence

ORD record
ord-548804b8b0344758893f2d65a8348415
Source dataset
uspto-grants-1995_05
Patent number
US05420138

Reaction notes

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