Ethanol → 2-Fluoro-6-(4-octyloxyphenyl)pyrazine

HRID 864264

반응식

HRID 864264 반응식
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH2:9]([O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:19][CH:20]=2)[N:3]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 232733782-Chloro-6-fluoropyrazine

생성물 1

HCID 218046342-Fluoro-6-(4-octyloxyphenyl)pyrazine수율 94.7%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 962Water용매

실험 절차

7.99 g (60.0 mmol) of 2-chloro-6-fluoropyrazine, 15.08 g (60.0 mmol) of 4-octyloxyphenylboronic acid, 12.78 g (120.0 mmol) of sodium carbonate and 0.72 g (0.6 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 2 hours in 400 ml of benzene, 300 ml of ethanol and 150 ml of water. The reaction mixture is partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, filtered and freed from the solvents, and the residue is purified by chromatography (silica gel/hexane: ethyl acetate = 8:2). 17.18 g of 2-fluoro-6-(4-octyloxyphenyl)pyrazine are obtained. ##STR15## 1c

후처리

  1. customThe reaction mixture is partitioned between aqueous sodium chloride solution and ether
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe residue is purified by chromatography (silica gel/hexane: ethyl acetate = 8:2)

출처 및 근거

ORD 기록
ord-6998e2e71ad14421b508456399b3d2bd
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05562859

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