Sodium Carbonate → 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 79613

반응식

HRID 79613 반응식
[Br:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>Cl>[Br:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 602052755-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine수율 28.2%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

5-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (2.0 g, 7.7 mmol) was placed in 6M HCl (30 mL) at room temperature. SnCl2 (7.29 g, 38.5 mmol) was then added, and the reaction was stirred for 30 minutes at room temperature. The reaction was then cooled to 0° C. and a saturated aqueous solution of Na2CO3 was added to raise the pH to 8. The reaction was then extracted with DCM (with minimal MeOH to aid solubility). The combined organic fractions were dried, filtered, and concentrated to give the crude product 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.50 g, 28.2% yield), which was used without purification.

후처리

  1. temperatureThe reaction was then cooled to 0° C.
  2. temperatureto raise the pH to 8
  3. extractionThe reaction was then extracted with DCM (with minimal MeOH to aid solubility)
  4. customThe combined organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-262e553a27c44f969cd6bf6fe0afe17a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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