Sodium Methoxide → 7-[(Methylsulfanyl)methyl]-1H-indole

HRID 561372Notes

Reaction equation

HRID 561372 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][S:18][CH3:19])[CH:10]=[CH:9]1)=O)(C)(C)C.C[O-].[Na+]>CO>[CH3:19][S:18][CH2:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[NH:8][CH:9]=[CH:10]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58392224HCID 58392224, compound

Product 1

HCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.16 g (4.18 mmol) of the compound from Example 7A were introduced into 23 ml of methanol, 26 ml (113 mmol) of a 25% strength methanolic sodium methanolate solution were added, and the mixture was stirred at RT overnight. Then ice-water was added, and the mixture was extracted with dichloromethane. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient) to result in 549 mg (74% of theory) of the title compound.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-b9c1050cb38e45e789e8595762e561af
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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