Sodium Carbonate → HCID 9845828, compound

HRID 1354173Notes

Reaction equation

HRID 1354173 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].Br[C:18]1[C:19]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)=[N:20][N:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=12.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.ClCCl>[F:37][C:33]1[CH:32]=[C:31]([C:19]2[C:18]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=3)=[C:22]3[CH:23]=[CH:24][C:25]([C:27]([F:29])([F:30])[F:28])=[CH:26][N:21]3[N:20]=2)[CH:36]=[CH:35][CH:34]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 132184-IodobenzenesulfonamideHCID 517044Potassium AcetateHCID 11772769HCID 11772769, compound

Product 1

HCID 9845828HCID 9845828, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-iodobenzenesulphonamide (651 mg); dipinacoldiborane (495 mg)2; potassium acetate (860 mg); and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride complex:dichloromethane (1:1) (50 mg); in DMF (5 ml) was heated under nitrogen at 80° for 1.5 h. To the cooled reaction mixture was added 3-bromo-2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridine (330 mg, 0.919 mmol), 2N Na2CO3 (4 ml) and tetrakis(triphenylphosphine)palladium(0) (40 mg) and the mixture heated at reflux under nitrogen for 18 hours. The cooled reaction mixture was poured into water (30 ml) and the suspension extracted with ethyl acetate (3×20 ml). The organic extracts were combined, dried (Na2SO4) and concentrated in vacuo. The residue was purified by SPE chromatography eluting with a gradient of cyclohexane:ethyl acetate (100:0 to 0:100, 10% step). Trituration of the concentrated fractions containing product with diethyl ether gave the title compound as a white solid (139 mg, 35%). MH+ 436

Workup

  1. customTo the cooled reaction mixture
  2. temperaturethe mixture heated
  3. temperatureat reflux under nitrogen for 18 hours
  4. customThe cooled reaction mixture
  5. extractionthe suspension extracted with ethyl acetate (3×20 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SPE chromatography
  9. washeluting with a gradient of cyclohexane:ethyl acetate (100:0 to 0:100, 10% step)
  10. additionTrituration of the concentrated fractions containing product with diethyl ether

Sources & evidence

ORD record
ord-c5e65e95c2524124a1ebc3921d4204db
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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