HCID 68960002, compound → HCID 57668015, compound

HRID 2191777Notes

Reaction equation

HRID 2191777 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[CH:19]=[C:18]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[CH:17]=[CH:16][C:8]=2[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[CH:19]=[C:18]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[CH:17]=[CH:16][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68960002HCID 68960002, compound

Product 1

HCID 57668015HCID 57668015, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid 10 mL was added to the obtained tert-butyl 2-(4-fluoroanilino)-4-(indolin-1-yl)benzoate, and it was stirred at room temperature for 2 hours and 10 minutes. The solvent was removed under reduced pressure, ethyl acetate and water were added to the obtained residue, and it was adjusted to pH6.5 with saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Diisopropyl ether was added to the obtained residue, solid matter was filtrated to give 2-(4-fluoroanilino)-4-(indolin-1-yl)benzoic acid 22 mg of a white solid.

Workup

  1. customThe solvent was removed under reduced pressure, ethyl acetate and water
  2. additionwere added to the obtained residue, and it
  3. customThe organic layer was separated
  4. washafter sequential washing with water and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue, solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-b4f75fd716bb4af3bfb656f4f5664192
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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