Water → 5-[3-(2,6-dichloropyridin-4-yl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 2172530ノート

反応式

HRID 2172530 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:14](SC)=[N:15][CH2:16][Si](C)(C)C)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)#[N:2].[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[N:25]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Cl:23][C:24]1[CH:29]=[C:28]([C:30]2([C:32]([F:33])([F:34])[F:35])[CH2:31][C:14]([C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[N:12][CH:11]=[N:10]4)=[C:3]([CH:4]=3)[C:1]#[N:2])=[N:15][CH2:16]2)[CH:27]=[C:26]([Cl:36])[N:25]=1

参加物

6

反応物 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66820051methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioateHCID 86664620Pyridine, 2,6-dichloro-4-[1-(trifluoromethyl)ethenyl]-

生成物 1

HCID 497871395-[3-(2,6-dichloropyridin-4-yl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the crude solution of methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate (Japanese patent application JP2008-143120) was added 2,6-dichloro-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine (0.15 g) and the resultant mixture was cooled to −10° C. Additionally, a solution of tetrabutylammonium fluoride (0.70 mL of 1.0 M in THF) in THF was added over 10 minutes under argon atmosphere. The reaction mixture was stirred for 30 minutes at the same temperature and returned to room temperature gradually, and then stirred 3 hours. Water was added to the reaction liquor, and aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous brine, and subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 5-[3-(2,6-dichloropyridin-4-yl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (0.14 g) at a yield of 46%.

後処理

  1. customreturned to room temperature
  2. stirringstirred 3 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe combined organic layers were washed with a saturated aqueous brine
  5. dry with materialsubsequently dried over magnesium sulfate
  6. filtrationAfter filtering the reaction mixture
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe resulting mixture was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-07a9c8c0fe2840a385a6c06973640899
出典データセット
uspto-grants-2015_06
特許番号
US09055749B2

反応ノート

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