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

HRID 600382Notes

Reaction equation

HRID 600382 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8a3e73bb27e34415a68166bfe6845dcb
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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