Trifluoroacetic acid → 5-Chloro-4-(((5-chloro-6-cyclopropylpyridin-3-yl)oxy)methyl)-2-fluorobenzoic acid

HRID 1525676Notes

Reaction equation

HRID 1525676 reaction equation
[Cl:1][C:2]1[C:3]([CH2:16][O:17][C:18]2[CH:19]=[N:20][C:21]([CH:25]3[CH2:27][CH2:26]3)=[C:22]([Cl:24])[CH:23]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[C:3]([CH2:16][O:17][C:18]2[CH:19]=[N:20][C:21]([CH:25]3[CH2:27][CH2:26]3)=[C:22]([Cl:24])[CH:23]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 89633279HCID 89633279, compound

Product 1

HCID 896191735-Chloro-4-(((5-chloro-6-cyclopropylpyridin-3-yl)oxy)methyl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 5-chloro-4-(((5-chloro-6-cyclopropylpyridin-3-yl)oxy)methyl)-2-fluorobenzoate (Preparation 26, 1.24 g, 3.01 mmol) in dichloromethane (22 mL) was added TFA (10.0 mL, 0.02 mol). The mixture was stirred under nitrogen at room temperature for 18 hours. Additional TFA (2.50 mL, 32.0 mmol) was added and stirring continued for 3 hours. The reaction mixture was evaporated under reduced pressure and the resulting residue dissolved in EtOAc (25 mL) and washed with 2M aqueous solution of HCl (25 mL). The resulting solid was filtered to afford the title compound (1.4 g, crude quant.) which was used with no further purification.

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. dissolutionthe resulting residue dissolved in EtOAc (25 mL)
  5. washwashed with 2M aqueous solution of HCl (25 mL)
  6. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-e73b0d51730a4acc91d74722f1d80874
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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