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

HRID 16417

反応式

HRID 16417 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ea0e983032304f259c08a3a0dfb9a679
出典データセット
uspto-grants-2010_06
特許番号
US07737153B2

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