Methyl chloroglyoxylate → 2-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

HRID 1157288노트

반응식

HRID 1157288 반응식
[F:1][C:2]1[CH:7]=[N:6][C:5]([NH2:8])=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].C(C1NC=C[N+]=1C)C.Cl[C:26](=[O:31])[C:27]([O:29]C)=[O:28]>O>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([F:1])=[C:3]2[C:11]([C:26](=[O:31])[C:27]([OH:29])=[O:28])=[CH:10][NH:9][C:4]=12

참가 물질

6

반응물 4

HCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) ChlorideHCID 159870184-fluoro-1H-pyrrolo[2,3-c]pyridin-7-amineHCID 17821953Ethylmethylimidazolium chloride

생성물 1

HCID 595111932-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-fluoro-1H-pyrrolo[2,3-c]pyridin-7-amine (2.26 g, 15 mmol) was added to a mixture of AlCl3 (12.0 g, 90.0 mmol) and ethylmethylimidazolium chloride (4.38 g, 30.0 mmol). Methyl chlorooxoacetate (3.6 mL, 30.0 mmol) was added slowly to the above solution and the mixture was stirred at rt for 3 h. Reaction flask was placed in an ice bath and water was slowly added until a white precipitate formed. The solid was collected by filtration and suspended in DMF. TEA (7 mL) was added and the mixture was stirred at rt for 1 h. Solvent was removed in vacuum. Chloroform (50 mL) was added and the solid was collected by filtration to afford 2-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid as a bright yellow solid (2.3g, 90% pure). LCMS: m/e 238 (M+H)+, ret time 0.96 min (method 3).

후처리

  1. customReaction flask
  2. customwas placed in an ice bath
  3. customformed
  4. filtrationThe solid was collected by filtration
  5. additionTEA (7 mL) was added
  6. stirringthe mixture was stirred at rt for 1 h
  7. customSolvent was removed in vacuum
  8. additionChloroform (50 mL) was added
  9. filtrationthe solid was collected by filtration

출처 및 근거

ORD 기록
ord-99b2c46de4de4afa8ccaf4d0497690db
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807671B2

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