Formic Acid → 5-(Trifluoromethyl)thiophene-2-sulfonamide
Reaction equation
S(C1C=CC(N2C(O[C:17]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[S:19][C:18]=3[S:26]([NH2:29])(=[O:28])=[O:27])=NN=N2)=CC=1)(=O)(=O)N.O.CCO.C(O)=O>C1C=CC=CC=1.[Pd]>[F:25][C:22]([F:23])([F:24])[C:20]1[S:19][C:18]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:17][CH:21]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3-[1-(4-sulfamoyl-phenyl)-1H-tetrazol-5-yloxy]-5-trifluoromethyl-thiophene-2-sulfonamide (210 mg, 0.47 mmol) in benzene (50 mL) is added H2O (2 mL), EtOH (3 mL), formic acid (2 mL) and 10% palladium on carbon (350 mg). The mixture is heated to 80° C. overnight. The reaction mixture is cooled to room temperature and diluted with benzene (50 mL). The reaction mixture is filtered. The benzene layer is dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with EtOAc:Hex (1:10) to afford the title compound (18 mg, 17%) as a white solid.
Workup
- temperatureThe reaction mixture is cooled to room temperature
- filtrationThe reaction mixture is filtered
- dry with materialThe benzene layer is dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude product is chromatographed on silica gel
- washeluting with EtOAc
Sources & evidence
- ORD record
- ord-ee4e6a5cc7b84991a32b0ade466db901
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250430B2
Reaction notes
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