Tetrahydrofuran → HCID 58706399, compound

HRID 2114171Notes

Reaction equation

HRID 2114171 reaction equation
C([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17]([C:19]2[C:20]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[C:11]([C:35](=[O:39])[N:36]([CH3:38])[CH3:37])[CH:10]=1)C1C=CC=CC=1.C1COCC1>[C].[Pd].CO>[CH3:37][N:36]([CH3:38])[C:35]([C:11]1[CH:10]=[C:9]([OH:8])[C:14]([F:15])=[CH:13][C:12]=1[NH:16][C:17]([C:19]1[C:20]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=2)=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:18])=[O:39]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58706418HCID 58706418, compound

Product 1

HCID 58706399HCID 58706399, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid (4-benzyloxy-2-dimethylcarbamoyl-5-fluorophenyl)amide (1.48 g) in a mixed solvent of THF (10 mL) and methanol (10 mL) was added 7.5% palladium carbon (200 mg). The mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. The reaction solution was filtered through a celite to remove the catalyst, and the filtrate was concentrated to give 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-5-fluoro-4-hydroxyphenyl)amide (1.09 g).

Workup

  1. filtrationThe reaction solution was filtered through a celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ef1a6716ca4247198ce2fac3178f720c
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

Loading…