Water → HCID 67108944, compound

HRID 2370988Notes

Reaction equation

HRID 2370988 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:18]2[C:19]([CH3:24])=[N:20][O:21][C:22]=2[CH3:23])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:27][N:28]([CH3:33])[S:29](Cl)(=[O:31])=[O:30].O>CN(C=O)C>[CH3:24][C:19]1[C:18]([C:10]2[N:11]([S:29]([N:28]([CH3:33])[CH3:27])(=[O:31])=[O:30])[C:12]3[C:17]([C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:22]([CH3:23])[O:21][N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 67108903HCID 67108903, compound2×

Product 1

HCID 67108944HCID 67108944, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole (the intermediate product of step (d) from Example 1, 35 mg, 0.11 mmol) was added to a suspension of NaH (25 mg, 60% in heptane) in DMF (dry, 0.7 ml) at 0° C. under nitrogen. The mixture was stirred at rt for 30 min and was then cooled to 0° C. again. Dimethylsulfamoyl chloride (2 eq) was added drop wise. The mixture was stirred at rt for 2 h, cooled to 0° C. and water was added to quench the reaction. Extraction with DCM using isolute phase separator and concentration of the combined organic layers afforded 2-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-N,N-dimethyl-1H-indole-1-sulfonamide in quantitative yield.

Workup

  1. temperaturewas then cooled to 0° C. again
  2. stirringThe mixture was stirred at rt for 2 h
  3. temperaturecooled to 0° C.
  4. customto quench
  5. customthe reaction
  6. extractionExtraction with DCM using isolute phase separator and concentration of the combined organic layers

Sources & evidence

ORD record
ord-fb01e0416dbf4496aab1f86af7568a01
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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