Potassium Carbonate → HCID 67008007, compound

HRID 564019Notes

Reaction equation

HRID 564019 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.S(Cl)(Cl)=O.C([O-])([O-])=[O:19].[K+].[K+].[NH:24]1[C:28]2=[N:29][CH:30]=[C:31]([NH2:33])[CH:32]=[C:27]2[CH:26]=[CH:25]1>C1C=CC=CC=1.C(#N)C>[CH3:4][C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[C:1]([NH:33][C:31]1[CH:32]=[C:27]2[CH:26]=[CH:25][NH:24][C:28]2=[N:29][CH:30]=1)=[O:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 747904-Nitro-o-toluic acidHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amine

Product 1

HCID 67008007HCID 67008007, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-methyl-4-nitrobenzoic acid (2 g, 11 mmol) in benzene (40 ml) was added thionyl chloride (2 ml) and refluxed for 3 h. The reaction mixture was concentrated, diluted with dry acetonitrile (20 ml). To this solution was added dry K2CO3 (2 g, 14 mmol) followed by a solution of 1H-Pyrrolo[2,3-b]pyridin-5-ylamine (example c), 1.4 g, 11 mmol) in acetonitrile (20 ml) and the reaction mixture and stirred for 16 h at RT. Solvent was removed under reduced pressure, diluted with water stirred for 15 min and filtered. The solid residue was washed with EtOAc to get 2.4 g of crude title product. LC-MS: (m/z 297)

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with dry acetonitrile (20 ml)
  4. customSolvent was removed under reduced pressure
  5. additiondiluted with water
  6. stirringstirred for 15 min
  7. filtrationfiltered
  8. washThe solid residue was washed with EtOAc

Sources & evidence

ORD record
ord-e8e8f8b6df1345b3b693f1e7f896e97b
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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