Water → HCID 14343212, compound

HRID 536630Notes

Reaction equation

HRID 536630 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1.O>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=1

Participants

7

Reactant 3

HCID 962WaterHCID 10821PhenylacetyleneHCID 27340872-Bromo-4-methylpyridine

Product 1

HCID 14343212HCID 14343212, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Phenylacetylene (15.4 mL) is added to a mixture of 2-bromo-4-methyl-pyridine (20.0 g), CuI (2.2 g), and Pd(PPh3)2Cl2 (4.1 g) in triethylamine (600 mL) kept under argon atmosphere. The mixture is stirred at ambient temperature overnight. Then, water is added and the resulting mixture is extracted with diethylether. The combined organic extracts are washed with brine and dried (MgSO4). The solvent is removed under reduced pressure and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1->4:1) to give the product as an oil.

Workup

  1. extractionthe resulting mixture is extracted with diethylether
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1->4:1)

Sources & evidence

ORD record
ord-8da996949ffb4e1f90c59af0b2a64b81
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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