N-(1,5-dimethyl-1H-pyrazol-3-yl)-3-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-5-[(phenylmethyl)oxy]benzamide → N-(1,5-dimethyl-1H-pyrazol-3-yl)-3-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-5-hydroxybenzamide
Reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9](=[O:30])[C:10]2[CH:15]=[C:14]([O:16]CC3C=CC=CC=3)[CH:13]=[C:12]([O:24][CH:25]([CH2:28][F:29])[CH2:26][F:27])[CH:11]=2)=[N:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9](=[O:30])[C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([O:24][CH:25]([CH2:26][F:27])[CH2:28][F:29])[CH:11]=2)=[N:3]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N-(1,5-dimethyl-1H-pyrazol-3-yl)-3-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-5-[(phenylmethyl)oxy]benzamide (1.89 mmol) in ethanol (30 mL) was treated with 10% palladium on carbon (78 mg, wetted with 1 mL ethanol). The flask was evacuated and filled with hydrogen and this procedure repeated a further 4 times. The mixture was left to stir at RT overnight under an atmosphere of hydrogen then the mixture filtered through Celite® and the cake washed with ethanol (50 mL) and ethyl acetate (50 mL). The combined organics were evaporated in vacuo to give the desired compound as a white foam (613 mg).
Workup
- customThe flask was evacuated
- additionfilled with hydrogen
- waitThe mixture was left
- filtrationthe mixture filtered through Celite®
- washthe cake washed with ethanol (50 mL) and ethyl acetate (50 mL)
- customThe combined organics were evaporated in vacuo
Sources & evidence
- ORD record
- ord-1bb175be12774abb872a5c60940b1acf
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642263B2
Reaction notes
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