Potassium Carbonate → HCID 11589308, compound

HRID 1009581Notes

Reaction equation

HRID 1009581 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH2:26][CH2:27][CH2:28]Cl)(=[O:25])=[O:24])=[CH:18][CH:17]=1)#[N:2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[O:24]=[S:23]1(=[O:25])[CH2:26][CH2:27][CH2:28][N:22]1[C:19]1[CH:20]=[CH:21][C:16]([C:4]2[N:5]([CH2:14][CH3:15])[C:6]3[C:11]([C:3]=2[C:1]#[N:2])=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=3)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59425226HCID 59425226, compound

Product 1

HCID 11589308HCID 11589308, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-chloropropane-1-sulfonic acid [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]amide, prepared above (3.65 g, 2.33 mmol) in DMF (100 mL) is treated with K2CO3 and heated at 70° C. for 2 h. After cooling to room temperature, the reaction mixture is diluted with H2O and extracted 3× with hot EtOAc. The hot organic layers are washed with warm H2O (3×) and saturated NaCl and dried and concentrated to a solid. Trituration (CH2Cl2/hexanes) gives 2.27 g (68%) of 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile as a light brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted 3× with hot EtOAc
  3. washThe hot organic layers are washed with warm H2O (3×) and saturated NaCl
  4. customdried
  5. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-353ce925383a488a868ee08e9e618182
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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