Phosphorus oxybromide → 4-bromo-2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]quinoline-6-carboxamide

HRID 70814

반응식

HRID 70814 반응식
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([NH:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([C:23]([F:35])([C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])[C:24]([F:27])([F:26])[F:25])=[CH:18][C:17]=3[CH2:36][CH3:37])=[O:14])[CH:9]=2)[N+:4]=1[O-])#[N:2].P(Br)(Br)([Br:41])=O.C(=O)([O-])O.[Na+]>C(#N)C>[Br:41][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([NH:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([C:23]([F:35])([C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])[C:24]([F:27])([F:26])[F:25])=[CH:18][C:17]=3[CH2:36][CH3:37])=[O:14])[CH:9]=2)[N:4]=[C:3]([C:1]#[N:2])[CH:12]=1

참가 물질

5

반응물 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 866729702-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]quinoline-6-carboxamide-1-oxide

생성물 1

HCID 866729724-bromo-2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]quinoline-6-carboxamide수율 43%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

2-Cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-quinoline-6-carboxamide-1-oxide (96 mg) was dissolved in acetonitrile, added with phosphoryl bromide (250 mg), and stirred at 100° C. for 5 hours. After cooling to room temperature, the reaction solution was poured into ice water and neutralized with sodium hydrogen carbonate. After extracting the mixture twice with ethyl acetate, the organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was removed by distillation under the reduced pressure. The resulting residues were purified by column chromatography to obtain 4-bromo-2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]quinoline-6-carboxamide (46 mg, 43%).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionAfter extracting the mixture twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was removed by distillation under the reduced pressure
  7. customThe resulting residues were purified by column chromatography

출처 및 근거

ORD 기록
ord-7bddf54d950647c9b202ef8fb1175e47
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822691B2

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