Potassium Carbonate → 4-[(6-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

HRID 16417

반응식

HRID 16417 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC(C)([O-])C.[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[N:28]=[C:27]2[NH:29][CH:30]=[CH:31][C:26]2=[C:25]([N+]([O-])=O)[CH:24]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:23]1[N:28]=[C:27]2[NH:29][CH:30]=[CH:31][C:26]2=[C:25]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=2[F:9])[CH:24]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 179793386-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 179792844-[(6-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

4-Amino-2-fluorophenol (0.77 g, 6.07 mmol) is dissolved in DMF. Potassium tert-butoxide (0.68 g, 6.07 mmol) is added, and the mixture is stirred at room temperature for 30 minutes. Powdered potassium carbonate (0.35 g, 2.53 mmol) and 1 g (5.06 mmol) of 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine (from example XXX) are then added successively. The mixture is stirred at 120° C. for 12 hours. After cooling, the mixture is diluted with ethyl acetate (200 ml). The suspension is filtered off with suction through Celite®, and the filtercake is washed with ethyl acetate. The solution is extracted successively with aqueous sodium bicarbonate solution and sodium chloride solution. The organic phase is dried over anhydrous magnesium sulfate and concentrated. The residue is purified by column chromatography (silica gel 60, mobile phase: DCM:acetone=5:1). This gives 0.95 g (67% of theory) of product.

후처리

  1. stirringThe mixture is stirred at 120° C. for 12 hours
  2. temperatureAfter cooling
  3. filtrationThe suspension is filtered off with suction through Celite®
  4. washthe filtercake is washed with ethyl acetate
  5. extractionThe solution is extracted successively with aqueous sodium bicarbonate solution and sodium chloride solution
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography (silica gel 60, mobile phase: DCM:acetone=5:1)

출처 및 근거

ORD 기록
ord-ea0e983032304f259c08a3a0dfb9a679
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737153B2

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