Ethyl Acetate → Benzenamine,4-[(6-chloro-3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoro-

HRID 16421

반응식

HRID 16421 반응식
C([N:4]1[C:8]2=[N:9][C:10]([Cl:14])=[CH:11][C:12](Cl)=[C:7]2[C:6]([CH3:15])=[CH:5]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([F:30])[CH:24]=1.C(OCC)(=O)C>CS(C)=O>[Cl:14][C:10]1[N:9]=[C:8]2[NH:4][CH:5]=[C:6]([CH3:15])[C:7]2=[C:12]([O:29][C:26]2[CH:27]=[CH:28][C:23]([NH2:22])=[CH:24][C:25]=2[F:30])[CH:11]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 179792891-acetyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 17979286Benzenamine,4-[(6-chloro-3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoro-

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

300 mg (1.16 mmol) of 1-acetyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine (from example XL) and 320 mg (2.32 mmol) of powdered potassium carbonate are suspended in 9 ml of DMSO. The mixture is degassed, and 442 mg (3.48 mmol) of 4-amino-2-fluorophenol are added. The mixture is heated at 120° C. for 4 hours. After addition of ethyl acetate, the mixture is filtered off with suction through CELITE (diatomaceous earth) and the filtercake is washed with ethyl acetate. The filtrate is extracted three times with sat. sodium bicarbonate solution and with sat. sodium chloride solution. The filtrate is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography (silica gel 60, mobile phase: DCM:methanol=50:1).

후처리

  1. customThe mixture is degassed
  2. filtrationthe mixture is filtered off with suction through CELITE (diatomaceous earth)
  3. washthe filtercake is washed with ethyl acetate
  4. extractionThe filtrate is extracted three times with sat. sodium bicarbonate solution
  5. dry with materialThe filtrate is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by column chromatography (silica gel 60, mobile phase: DCM:methanol=50:1)

출처 및 근거

ORD 기록
ord-f54b7a1f971e4a7496946caf6e8bee25
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737153B2

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