N,N'-Dimethylethylenediamine → 1-(4-Fluoro-phenyl)-6-methanesulfonyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 2382963Notes

Reaction equation

HRID 2382963 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21](Br)[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CNCCNC.[CH3:39][S:40]([O-:42])=[O:41].[Na+]>[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O.CS(C)=O>[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21]([S:40]([CH3:39])(=[O:42])=[O:41])[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

Product 1

HCID 581387781-(4-Fluoro-phenyl)-6-methanesulfonyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide (0.07 g, 0.1 mmol), copper(II) triflate (0.05 g, 0.1 mmol), N,N′-dimethylethylenediamine (0.04 mL, 0.4 mmol), sodium methanesulfinate (0.02 g, 0.2 mmol) was charged in a sealed tube with DMSO (5 mL). The tube was capped and the solution was degassed with argon for 5 minutes. The mixture was heated in a microwave at 110° C. for 40 minutes and cooled to room temperature. The solution was diluted with ethyl acetate (30 mL) and washed with saturated aqueous ammonium chloride (10 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL) and dried over sodium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 20-50% ethyl acetate in hexanes to afford the title compound.

Workup

  1. customThe tube was capped
  2. customthe solution was degassed with argon for 5 minutes
  3. temperaturecooled to room temperature
  4. additionThe solution was diluted with ethyl acetate (30 mL)
  5. washwashed with saturated aqueous ammonium chloride (10 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 20-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c196fb951e7546beb297090ec1eaa312
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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