Trifluoroacetic acid → HCID 57667893, compound

HRID 2191758Notes

Reaction equation

HRID 2191758 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[CH:29]=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:19]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH:18]=3)=[CH:16][C:11]=2[CH:10]=[CH:9]1>>[S:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[CH:29]=[CH:28][C:20]([C:21]([OH:23])=[O:22])=[C:19]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH:18]=3)=[CH:16][C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68964188HCID 68964188, compound

Product 1

HCID 57667893HCID 57667893, compound

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. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d219be163b9b4b42a224a682f51a4756
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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