HCID 67041861, compound → HCID 67041564, compound

HRID 62728Notes

Reaction equation

HRID 62728 reaction equation
[CH2:1]([O:3][C:4]1[CH:30]=[CH:29][C:7]([C:8]([NH:10][C:11]2[CH:26]=[C:25]([F:27])[C:14]([C:15]([O:17]CC3C=CC=CC=3)=[O:16])=[C:13]([F:28])[CH:12]=2)=[O:9])=[CH:6][C:5]=1[C:31]([F:34])([F:33])[F:32])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]1[CH:30]=[CH:29][C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([F:28])[C:14]([C:15]([OH:17])=[O:16])=[C:25]([F:27])[CH:26]=2)=[O:9])=[CH:6][C:5]=1[C:31]([F:33])([F:34])[F:32])[CH3:2]

Participants

4

Reactant 1

HCID 67041861HCID 67041861, compound

Product 1

HCID 67041564HCID 67041564, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 4-(4-ethoxy-3-(trifluoromethyl)benzamido)-2,6-difluorobenzoate (4) (25 mg, 52 μmol) was dissolved in methanol (10 mL) and was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 25° C. under H2 (10 bar). The solvent was removed in vacuo to afford 4-(4-ethoxy-3-(trifluoromethyl)benzamido)-2,6-difluorobenzoic acid (XXX-02) (20 mg, 97%) as a white solid: m/z 388.1 (M−H)− (ES−). 1H NMR (400 MHz, MeOD) δ: 8.23 (1H, d), 8.19 (1H, dd), 7.53 (2H, dt), 7.30 (1H, d), 4.26 (2H, q), 1.46 (3H, t).

Workup

  1. customat 25° C.
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f4c782756ac644ecbaad2e18263e4e3d
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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