Trimethylsilylacetylene → 1-(5Methylpyridin-2-yl)-2-(2,3-difluoro-4-ethoxyphenyl) acetylene

HRID 974160Notes

Reaction equation

HRID 974160 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[CH:9])=[N:6][CH:7]=1.CC1C=CC(Br)=NC=1.C[Si](C#C)(C)C.I[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[C:27]([F:34])[C:26]=1[F:35]>[Pd].[Cu]I.C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[C:27]([F:34])[C:26]=2[F:35])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 66111TrimethylsilylacetyleneHCID 5642162-Bromo-5-methylpyridineHCID 134006342-Ethynyl-5-methylpyridineHCID 220080781-Ethoxy-2,3-difluoro-4-iodobenzene

Product 1

HCID 179780101-(5Methylpyridin-2-yl)-2-(2,3-difluoro-4-ethoxyphenyl) acetylene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 0.01 mol of 5-methylpyridin-2-yl-acetylene (which can be prepared from 5-methyl-2-bromopyridine by reaction with trimethylsilyl-acetylene and Pd catalyst and subsequent splitting off of the trimethylsilyl group), 0.01 mol of 4-iodo-2,3-difluorophenetole (for the preparation, see Example 9), 30 ml of triethylamine, 0.2 mmol of Pd catalyst and 0.1 mmol of CuI is stirred at room temperature for 24 hours. The reaction mixture is diluted with petroleum ether and filtered over silica gel. Evaporation and purification give 1-(5methylpyridin-2-yl)-2-(2,3-difluoro-4-ethoxyphenyl) acetylene.

Workup

  1. customfor the preparation
  2. filtrationfiltered over silica gel
  3. customEvaporation and purification

Sources & evidence

ORD record
ord-e5c2e1a1e50d4ddf8f8539b7d732b4a3
Source dataset
uspto-grants-1991_11
Patent number
US05068053

Reaction notes

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