2-Bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine → 2-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyrazine

HRID 864266

反応式

HRID 864266 の反応式
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:12]1[C:17]([F:18])=[N:16][C:15]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:21][CH:20]=2)=[CH:14][N:13]=1>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[F:18][C:17]1[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:13][CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:21][CH:20]=2)[N:16]=1

参加物

5

反応物 2

HCID 218046332-Bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazineHCID 178443577HCID 178443577、化合物

生成物 1

HCID 194182962-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyrazine

試薬・触媒・溶媒 2

HCID 178418745HCID 178418745、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

7.95 mmol of freshly prepared octylmagnesium bromide in 30 ml of tetrahydrofuran are added dropwise at -10° C. to 2.00 g (5.3 mmol) of 2-bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine and 0.03 g (0.06 mmol) of [1,3-bis-(diphenylphosphino)propane]nickel(II) chloride in 30 ml of tetrahydrofuran, and the reaction mixture is stirred overnight, during which it warms to room temperature. The reaction mixture is partitioned between aqueous ammonium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, filtered and freed from the solvent, and the mixture is purified by chromatography (silica gel/dichloromethane: hexane = 7:3). 1.12 g of 2-fluoro-3-octyl-6-(4-octyloxyphenyl)pyrazine are obtained. ##STR17## The compound has the following phase sequence:

後処理

  1. customwarms to room temperature
  2. customThe reaction mixture is partitioned between aqueous ammonium chloride solution and ether
  3. washthe organic phase is washed with aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe mixture is purified by chromatography (silica gel/dichloromethane: hexane = 7:3)

出典と根拠

ORDレコード
ord-acb452673ccb482b9d8959684f9ae9c6
出典データセット
uspto-grants-1996_10
特許番号
US05562859

関連ノート

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