Potassium Carbonate → HCID 13508373, compound

HRID 128833Notes

Reaction equation

HRID 128833 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)N(S(C2C=CC=CC=2)(=O)=O)C=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:34][S:35]SC.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.O>[CH2:1]([N:8]1[C:18]2[C:19](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:11]=[C:9]1[S:35][CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 12232Dimethyl DisulfideHCID 14943551HCID 14943551, compoundHCID 178418339Butyllithium

Product 1

HCID 13508373HCID 13508373, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of the above N-benzyl-1-(phenylsulfonyl)indole -3-carboxamide [XXIV: R8 =CH2Ph] (4.2 g, 11 mmol) in dry THF (200 mL) was treated at -78° C. with a solution of 2.5M n-BuLi in hexanes (9.1 mL, 23 mmol), and the stirred mixture was allowed to warm to -20° C. for 15 minutes, before being recooled to -78° C., when it was treated with methyldisulfide (2.5 mL, 28 mmol). The mixture was allowed to warm to 20° C., then quenched with water (25 mL). Volatiles were removed under reduced pressure, and the residue was extracted with EtOAc. Workup of the organic layer gave a crude product. This was dissolved in MeOH (300 mL), mixed with a solution of K2CO3 (6.9 g, 50 mmol) in water (125 mL), and heated under gentle reflux under N2 for 2 hours to ensure complete hydrolysis of the phenylsulfonyl group (J. Org. Chem. 1985;50:5451-5457). MeOH was removed under reduced pressure, and the residue was diluted with water and extracted with CH2Cl2. Chromatography of the resulting oil on Al2O3 (eluting with CH2Cl2) gave N-benzyl-2-(methylthio)indole -3-carboxalnide [XXV: R8 =CH2Ph] (2.8 g, 88% yield) as an oil.

Workup

  1. custombefore being recooled to -78° C.
  2. temperatureto warm to 20° C.
  3. customquenched with water (25 mL)
  4. customVolatiles were removed under reduced pressure
  5. extractionthe residue was extracted with EtOAc
  6. customWorkup of the organic layer gave a crude product
  7. temperatureheated
  8. temperatureunder gentle reflux under N2 for 2 hours
  9. customhydrolysis of the phenylsulfonyl group (J. Org. Chem. 1985;50:5451-5457)
  10. customMeOH was removed under reduced pressure
  11. additionthe residue was diluted with water
  12. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-3fbd4ec1c6c54b989b7c24c2643f4bee
Source dataset
uspto-grants-1995_11
Patent number
US05464861

Reaction notes

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