Water → HCID 14343212, compound

HRID 1616644Notes

Reaction equation

HRID 1616644 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 diethyl ether. 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 diethyl ether
  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-b991d1a7b32340eea1ceef4a561ee61e
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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