Toluene → HCID 68960712, compound

HRID 2191762Notes

Reaction equation

HRID 2191762 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:47]=[CH:46][CH:45]=[C:44]2[C:40]=1[CH:41]=[CH:42][NH:43]2.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>[F:8][C:9]1[CH:37]=[CH:36][C:12]([NH:13][C:14]2[CH:26]=[C:25]([C:39]3[CH:47]=[CH:46][CH:45]=[C:44]4[C:40]=3[CH:41]=[CH:42][NH:43]4)[CH:24]=[CH:23][C:15]=2[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[CH:11][CH:10]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 6764944-BromoindoleHCID 68962276HCID 68962276, compound

Product 1

HCID 68960712HCID 68960712, compound

Reagents, catalysts & solvents 4

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

Procedure

To toluene 1.6 mL solution of tert-butyl 2-(4-fluoroanilino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 60 mg were added ethanol 0.60 mL, water 0.30 mL, 4-bromoindole 0.034 mL, sodium hydrogen carbonate 30 mg and tetrakis(triphenylphosphine)palladium(0) 8.4 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 5 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=5:1] to give tert-butyl 2-(4-fluoroanilino)-4-(1H-indol-4-yl)benzoate.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 5 hours
  3. filtrationinsoluble matter was filtrated
  4. customThe organic layer was separated
  5. washafter washing with saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-49d56b8fb5b643219ebf1de6a6e01445
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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