hydroxylamine-O-sulfonic acid → 1-amino-5-fluoro-1H-indole-3-sulfonic acid dimethylamide
Reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][CH:7]=1)(=[O:5])=[O:4].[NH2:17]OS(O)(=O)=O>CN(C=O)C>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]([NH2:17])[CH:7]=1)(=[O:4])=[O:5]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A solution of 5-fluoro-1H-indole-3-sulfonic acid dimethylamide (1.24 g) in dry DMF (50 mL) is cooled to 0° C. and treated portion wise with 60% MaH oil dispersion (3.07 g). The mixture is stirred at 0° C. for 30 min. Hydroxylamine-O-sulfonic acid (2.9 g) is added portion wise and the mixture is warmed to rt and stirred for 5 h. The reaction mixture is poured onto ice/water and extracted with EtOAc. The organic layer is separated, washed water and brine, dried (MgSO4) filtered and concentrated in vacuo. The residue is triturated with ether. The solid is collected by filteration to afford 1-amino-5-fluoro-1H-indole-3-sulfonic acid dimethylamide (0.53 g, 41%). MS: 258 (M+H).
Workup
- additiontreated portion wise with 60% MaH oil dispersion (3.07 g)
- temperaturethe mixture is warmed to rt
- stirringstirred for 5 h
- additionThe reaction mixture is poured onto ice/water
- extractionextracted with EtOAc
- customThe organic layer is separated
- washwashed water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue is triturated with ether
- customThe solid is collected by filteration
Sources & evidence
- ORD record
- ord-8933337fb724439a9ef269b62c7a2518
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258130B2
Reaction notes
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