Toluene → HCID 68964078, compound

HRID 2191772Notes

Reaction equation

HRID 2191772 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:37]=[CH:36][C:12]([NH:13][C:14]2[CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[CH:24]=[CH:23][C:15]=2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1.Br[C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH2:48])(=[O:47])=[O:46])=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>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.C(OCC)(=O)C.C(O)C>[NH2:48][S:45]([C:42]1[CH:43]=[CH:44][C:39]([C:25]2[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])=[C:14]([NH:13][C:12]3[CH:36]=[CH:37][C:9]([F:8])=[CH:10][CH:11]=3)[CH:26]=2)=[CH:40][CH:41]=1)(=[O:47])=[O:46]

Participants

9

Reactant 4

HCID 1140TolueneHCID 696964-BromobenzenesulfonamideHCID 516892Sodium BicarbonateHCID 68962276HCID 68962276, compound

Product 1

HCID 68964078HCID 68964078, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To toluene 3.0 mL solution of tert-butyl 2-(4-fluoroanilino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 0.15 g were added ethanol 0.90 mL, water 0.45 mL, 4-bromobenzenesulfonamide 85 mg, sodium hydrogen carbonate 0.10 g and tetrakis(triphenylphosphine)palladium(0) 21 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, and ethyl acetate and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=2:1] to give tert-butyl 4-(4-(aminosulfonyl)phenyl)-2-(4-fluoroanilino)benzoate.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 2 hours
  3. customThe organic layer was separated
  4. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6d5e35a84d5249029828df1e0a2e4f85
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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