Water → 7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid dimethylamide

HRID 600382노트

반응식

HRID 600382 반응식
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C]=O.O.C(OCC)(=O)C.[CH3:26][N:27]([CH3:30])[CH:28]=[O:29]>[Cl-].[Cl-].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd+2]>[CH3:26][N:27]([CH3:30])[C:28]([C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1)=[O:29]

참가 물질

7

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-oneHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 441999597-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid dimethylamide수율 32%

시약·촉매·용매 1

HCID 178478645Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

실험 절차

1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (50 mg, 0.177 mmol) was dissolved in N,N-dimethylformamide and the flask was purged with carbon monoxide. Dimethylamine (0.32 ml of a 5.5M ethanol solution) was added followed by palladium bis(diphenylphosphino)ferrocene dichloride, dichloromethane complex (14 mg, 0.0177 mmol). A carbon monoxide-filled balloon was attached and the flask was stirred in a 100 C bath for 48 hrs. The reaction was worked up by addition of water and ethyl acetate. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined ethyl acetate layers were washed with water and then saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated to a residue. The residue was purified by silica gel chromatography (methanol/dichloromethane) to give 16 mg (32%) of product. MP=98-101 C, (M+H)+=275.

후처리

  1. customthe flask was purged with carbon monoxide
  2. additionDimethylamine (0.32 ml of a 5.5M ethanol solution) was added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice more with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water
  6. dry with materialsaturated sodium chloride solution, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to a residue
  9. customThe residue was purified by silica gel chromatography (methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-8a3e73bb27e34415a68166bfe6845dcb
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902197B2

반응 노트

불러오는 중…