Potassium Carbonate → HCID 67007228, compound

HRID 564020Notes

Reaction equation

HRID 564020 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.C([O-])([O-])=O.[K+].[K+].[NH:25]1[C:29]2=[N:30][CH:31]=[C:32]([NH2:34])[CH:33]=[C:28]2[CH:27]=[CH:26]1>C1C=CC=CC=1.C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH:34][C:32]1[CH:33]=[C:28]2[CH:27]=[CH:26][NH:25][C:29]2=[N:30][CH:31]=1)=[O:6]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic AcidHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amine

Product 1

HCID 67007228HCID 67007228, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-fluoro-5-nitrobenzoic acid from example d-2 (2 g, 9.1 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 dry K2CO3, (2 g, 14 mmol) was added, followed by a solution of 1H-Pyrrolo[2,3-b]pyridin-5-ylamine (example c), 1.2 g, 9.1 mmol) in acetonitrile (20 ml) and the reaction mixture was stirred for 16 h at RT. Filtered the reaction mixture through cintered faunal. The residue was washed with dry acetonitrile several times. Solvent was removed under reduced pressure, 2.8 g of the crude title product. LC-MS: (m/z 335)

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with dry acetonitrile (20 ml)
  4. filtrationFiltered the reaction mixture through cintered faunal
  5. washThe residue was washed with dry acetonitrile several times
  6. customSolvent was removed under reduced pressure, 2.8 g of the crude title product

Sources & evidence

ORD record
ord-0782de414d31495f8e81ab4a9d9b4411
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

Loading…