2,2,6,6-Tetramethylpiperidine → 2-Bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine

HRID 864265노트

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HRID 864265 반응식
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[F:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][CH:24]=2)[N:18]=1.[Br:38]Br>CCCCCC.O1CCCC1>[Br:38][C:22]1[C:17]([F:16])=[N:18][C:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][CH:24]=2)=[CH:20][N:21]=1

참가 물질

7

반응물 4

HCID 130352,2,6,6-TetramethylpiperidineHCID 24408BromineHCID 218046342-Fluoro-6-(4-octyloxyphenyl)pyrazineHCID 178418339Butyllithium

생성물 1

HCID 218046332-Bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

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온도
-78 °C

실험 절차

3.50 g (24.8 mmol) of 2,2,6,6-tetramethylpiperidine and 15.50 ml (24.80 mmol) of 1.6 M n-butyllithium solution in hexane are stirred at 0° C. for 0.5 hour in 80 ml of tetrahydrofuran, 250 ml of tetrahydrofuran are added, and the mixture is cooled to -78° C. 5.00 g (16.5 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyrazine in 150 ml of tetrahydrofuran and, after the mixture has been stirred for one hour, 0.85 ml of bromine are subsequently added dropwise at -78C. The reaction mixture is stirred overnight, during which it warms to room temperature, and is partitioned between ether and aqueous sodium chloride solution, the aqueous phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, filtered and freed from the solvent, and the residue is purified by chromatography (silica/hexane: ethyl acetate = 9:1). 4.68 g of 2-bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine are obtained. ##STR16## 1d

후처리

  1. customwarms to room temperature
  2. customis partitioned between ether and aqueous sodium chloride solution
  3. washthe aqueous phase is washed with aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe residue is purified by chromatography (silica/hexane: ethyl acetate = 9:1)

출처 및 근거

ORD 기록
ord-4af11b7138bf4c79a2c71c4cbb5fe6c7
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05562859

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