N-[4-(2-Benzyloxy-4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide → N-[4-(4-Fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878026Notes

Reaction equation

HRID 878026 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]([CH3:39])[C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:15][C:13]1[CH:12]=[CH:11][C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N:22]([CH3:39])[C:23](=[O:38])[C:24]2[CH:25]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=2)=[C:9]([OH:8])[CH:14]=1

Participants

5

Reactant 2

HCID 60197400N-[4-(2-Benzyloxy-4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 136209610N-[4-(4-Fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamideYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[4-(2-benzyloxy-4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide (65 mg, 0.118 mmol, example 43) in MeOH (10 mL) was purged with argon for 20 minutes before 10% Pd—C (10 mg) was added. The resulting reaction mixture was hydrogenated under balloon pressure hydrogen at 25° C. for 16 hours. The reaction mixture was filtered through a bed of celite and the residue was further washed with EtOAc. The combined filtrate was concentrated in vacuo, and the crude material thus obtained was purified by column chromatography over silica gel (25-35% EtOAc in n-hexane) to give 45 mg of the desired compound. Off-white solid (60%). MS (ESI): m/z=459.0 [M+H]+.

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. filtrationThe reaction mixture was filtered through a bed of celite
  4. washthe residue was further washed with EtOAc
  5. concentrationThe combined filtrate was concentrated in vacuo
  6. customthe crude material thus obtained
  7. customwas purified by column chromatography over silica gel (25-35% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-2a64410e55e64f6f843a4bf806b56d23
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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