Triethylamine → 4-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile

HRID 2220477Notes

Reaction equation

HRID 2220477 reaction equation
[C:1]([C:3]1[NH:4][CH:5]=[C:6](I)[CH:7]=1)#[N:2].C(N(CC)CC)C.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[CH:24])[CH:18]=1>CN(C)C=O.C(OCC)(=O)C.[Cu]I>[Br:16][C:17]1[CH:18]=[C:19]([C:23]#[C:24][C:6]2[CH:7]=[C:3]([C:1]#[N:2])[NH:4][CH:5]=2)[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 114808181-Bromo-3-ethynylbenzeneHCID 132203124-Iodo-1H-pyrrole-2-carbonitrile

Product 1

HCID 686993714-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrileYield 99%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The dimethylformamide was vigorously deoxygenated with nitrogen gas before use in this reaction. To a solution of 2-cyano-4-iodopyrrole (2.30 g, 10.52 mmol) in dimethylformamide was added dichloropalladium(II) bistriphenylphosphine (185 mg), copper(I) iodide (50 mg) and finally triethylamine (3.85 mL). After stirring ten minutes, 1-bromo-3-ethynyl-benzene (2.38 g, 13.15 mmol) was added. This mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and washed with 2% aqueous lithium chloride and 5% aqueous sodium chloride. The organic phase was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 20% ethyl acetate/hexane) to afford 4-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile as a yellow solid, 2.84 g, 99% yield.

Workup

  1. customThe dimethylformamide was vigorously deoxygenated with nitrogen gas before use in this reaction
  2. stirringThis mixture was stirred overnight at room temperature under nitrogen atmosphere
  3. washwashed with 2% aqueous lithium chloride and 5% aqueous sodium chloride
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e9c45ccd47a34910befd549617018d77
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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