Ammonia → 2-(2-ethylsulfanyl-phenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine

HRID 923766노트

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HRID 923766 반응식
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]([CH3:20])[C:13]2=[N:14][CH:15]=[C:16](I)[CH:17]=[C:12]2[N:11]=1)[CH3:2].[F:21][C:22]([F:33])([F:32])[C:23]([F:31])([F:30])[C:24]([F:29])([F:28])C([O-])=O.[Na+].C(=O)([O-])O.[Na+].N>[Cu](I)I.C1(C)C(C)=CC=CC=1.CN1C(=O)CCC1>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]([CH3:20])[C:13]2=[N:14][CH:15]=[C:16]([C:24]([F:29])([F:28])[C:23]([F:31])([F:30])[C:22]([F:33])([F:32])[F:21])[CH:17]=[C:12]2[N:11]=1)[CH3:2]

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 23678859Sodium perfluorobutanoateHCID 679815902-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine

생성물 1

HCID 867082162-(2-ethylsulfanyl-phenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine수율 34.3%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 7237O-Xylene용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
150 °C

실험 절차

A mixture of 2-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (311 mg), copper iodide (1.5 g), sodium heptafluorobutyrate (1.8 g), NMP (5 ml), and xylene (25 ml) was stirred with heating at 150° C. for 12 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution and 28% aqueous ammonia were poured, and extracted with tart-butyl methyl ether. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 118 mg of 2-(2-ethylsulfanyl-phenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 128).

후처리

  1. temperatureInto the reaction mixture cooled to room temperature
  2. extractionextracted with tart-butyl methyl ether
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ae436b68d7e846088cab055ea95c7b40
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278983B2

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