Methyl p-toluenesulfonate → HCID 19800195, compound

HRID 1646957Notes

Reaction equation

HRID 1646957 reaction equation
[C:1]1([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[K+].S(C1C=CC(C)=CC=1)([O:28][CH3:29])(=O)=O>CN(C=O)C.ClCCl>[CH3:29][O:28][C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]=1[S:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 82127Potassium hydrideHCID 19800209HCID 19800209, compound

Product 1

HCID 19800195HCID 19800195, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add 1,3-dihydro-N-phenyl-3-(phenylthio)-2H-pyrrolo(2,3-b)pyridine (4.0 g, 12.6 mmole) portionwise to potassium hydride (KH) (1.73 g of 35 weight-percent KH in oil, washed with hexane, 15.1 mmole) in dry DMF (50 mL) at 0° C. under a nitrogen atmosphere. Stir for 45 minutes at 0° C. Add methyl tosylate(3.04 g, 16.3 mmole), and warm the reaction mixture up to room temperature slowly. Stir for 16 hours at room temperature. Remove DMF by high vacuum distillation. Add saturated aqueous NH4Cl (150 mL) and extract with ethyl acetate. Wash the organic extracts with saturated aqueous NaCl, dry with MgSO4, filter and rotoevaporate to give an oil. Dissolve oil in dichloromethane and chromatograph on silica gel, eluting with ethyl acetate:hexane (1:6). Combine appropriate fractions and concentrate under reduced pressure to give an oil. Crystallize the oil with diethyl ether-hexane to give the title compound as a white solid (1.05 g, m.p.=86°-87.5° C.).

Workup

  1. stirringStir for 16 hours at room temperature
  2. distillationRemove DMF by high vacuum distillation
  3. extractionAdd saturated aqueous NH4Cl (150 mL) and extract with ethyl acetate
  4. washWash the organic extracts with saturated aqueous NaCl
  5. dry with materialdry with MgSO4
  6. filtrationfilter
  7. customrotoevaporate to give an oil
  8. washchromatograph on silica gel, eluting with ethyl acetate:hexane (1:6)
  9. concentrationCombine appropriate fractions and concentrate under reduced pressure
  10. customto give an oil
  11. customCrystallize the oil with diethyl ether-hexane

Sources & evidence

ORD record
ord-40a45035b78c4cc0957c8418643c975b
Source dataset
uspto-grants-1993_01
Patent number
US05182289

Reaction notes

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