Dichloromethane → 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 408159노트

반응식

HRID 408159 반응식
[Cl: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.[OH-].[Na+].C(Cl)Cl>Cl>[Cl: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

6

반응물 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 602052745-chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 581955655-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine수율 77.4%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

5-Chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (1.20 g, 5.57 mmol) was placed in 6M HCl (30 mL). SnCl2 (5.28 g, 27.8 mmol) was then added, and the reaction was stirred for 30 minutes at room temperature. The reaction was then poured into a mixture of 1M NaOH and ice. The resulting suspension was then raised to a pH of 8 and then extracted with 3:1 DCM:i-PrOH. The combined organic fractions were dried, filtered, and concentrated to give the crude product, which was triturated with 10:1 hexanes:DCM to give the product 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.8 g, 77% yield).

후처리

  1. temperatureThe resulting suspension was then raised to a pH of 8
  2. extractionextracted with 3:1 DCM
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas triturated with 10:1 hexanes

출처 및 근거

ORD 기록
ord-20b5482eb009459ab486c73de3f7c3c4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08758830B2

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