Potassium Carbonate → HCID 21833804, compound

HRID 1741056Notes

Reaction equation

HRID 1741056 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([SH:14])=[C:10]([I:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:15](=O)([O-])[O-].[K+].[K+].Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1CCl>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:14][CH2:15][C:25]3[CH:24]=[CH:23][N:22]=[CH:27][CH:26]=3)=[C:10]([I:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 10495844HCID 10495844, compound

Product 1

HCID 21833804HCID 21833804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Acetyl-2,3-dihydro-6-iodo-1H-indol-5-thiol (D49) (0.346 g, 1.08 mmol) in dry DMF (5 ml) was treated with potassium carbonate (0.374 g, 3.71 mmol) followed by picolyl chloride hydrochloride (0.186 g, 1.13 mmol). After 65 h stirring at room temp. the reaction mixture was evaporated under reduced pressure and was partitioned between dichloromethane and water. The aqueous layer was then extracted with dichloromethane and the combined organic layers were then dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a pale brown solid which was dried in vacuo (0.392 g, 89%).

Workup

  1. customwas evaporated under reduced pressure
  2. customwas partitioned between dichloromethane and water
  3. extractionThe aqueous layer was then extracted with dichloromethane
  4. dry with materialthe combined organic layers were then dried (Na2SO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8c0240e819124e68b43e4e73608cbf9b
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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