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

HRID 974160
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HRID 974160 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 23938
Palladium
촉매
2회
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 8471Triethylamine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e5c2e1a1e50d4ddf8f8539b7d732b4a3
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05068053

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