N-methyl-2-pyrrolidone → 2-(2-ethylsulfanylphenyl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine

HRID 533614

반응식

HRID 533614 반응식
Br[C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17][CH2:18][CH3:19])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.CN1C(=O)CCC1.[F:28][C:29]([F:37])([F:36])[C:30]([F:35])([F:34])C([O-])=O.[Na+].C(=O)([O-])O.[Na+]>[Cu](I)I.C1(C)C(C)=CC=CC=1>[CH2:18]([S:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=[C:2]([C:30]([F:35])([F:34])[C:29]([F:37])([F:36])[F:28])[CH:3]=[C:4]2[N:10]=1)[CH3:19]

참가 물질

7

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온도
170 °C

실험 절차

A mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (500 mg), NMP (24 ml), xylene (10 ml), copper iodide (1.1 g), and sodium pentafluoropropionate (1.1 g) was heated to 170° C., and stirred with heating for 3 days. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 43 mg of 2-(2-ethylsulfanylphenyl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 55).

후처리

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

출처 및 근거

ORD 기록
ord-0149b457e018428895eb4c96e6a89f6d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853238B2

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