Toluene → HCID 68964188, compound

HRID 2191757Notes

Reaction equation

HRID 2191757 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:40]=[CH:41][C:42]2[S:46][CH:45]=[CH:44][C:43]=2[CH:47]=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>[S:46]1[C:42]2[CH:41]=[CH:40][C:39]([C:25]3[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])=[C:14]([NH:13][C:12]4[CH:36]=[CH:37][C:9]([F:8])=[CH:10][CH:11]=4)[CH:26]=3)=[CH:47][C:43]=2[CH:44]=[CH:45]1

Participants

9

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27765785-Bromo-1-benzothiopheneHCID 68962276HCID 68962276, compound

Product 1

HCID 68964188HCID 68964188, 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 79 mg were added ethanol 0.60 mL, water 0.30 mL, 5-bromobenzothiophene 61 mg, sodium hydrogen carbonate 48 mg and tetrakis(triphenylphosphine)palladium(0) 11 mg at room temperature, and it was heated and refluxed for 6 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 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 [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=5:1] to give tert-butyl 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoate. Trifluoroacetic acid 5.0 mL was added to the obtained tert-butyl 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 80-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoic acid 16 mg of a yellow solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 6 hours
  3. customThe organic layer was separated
  4. customcollected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washing with saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f3860910ee914111803497ed57c1c993
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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