Methyl p-toluenesulfonate → HCID 22467256, compound

HRID 381330Notes

Reaction equation

HRID 381330 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]([C:18]3[CH:26]=[C:25]([O:27][CH3:28])[C:21]4[O:22][CH2:23][O:24][C:20]=4[CH:19]=3)[C:14]([O:16][CH3:17])=[O:15])=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[C:29]1(C)C=CC(S(OC)(=O)=O)=CC=1>CN(C)C=O>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]([C:18]3[CH:26]=[C:25]([O:27][CH3:28])[C:21]4[O:22][CH2:23][O:24][C:20]=4[CH:19]=3)[C:14]([O:16][CH3:17])=[O:15])=[CH:9][N:10]2[CH3:29])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 22467252HCID 22467252, compound

Product 1

HCID 22467256HCID 22467256, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (289 mg of a 60% dispersion in paraffin wax) was added in portions to a stirred solution of methyl 2-(6-bromo-1H-3-indolyl)-2-(7-methoxy-1,3-benzodioxol-5-yl)acetate (from step (c), 2.7 g, 6.5 mmol) in anhydrous dimethylformamide (20 ml) at 0° C. under a nitrogen atmosphere. After 30 minutes, methyl p-toluenesulphonate (1.34 g, 7.2 mmol) was added. After a further 1 hour the mixture was partitioned between diethyl ether and water. The organic layer was separated and washed twice with water. The organic layer was dried (magnesium sulphate) and the solvent was removed in vacuo. The residue was purified by flash column chromatography (using 30% hexane, 70% dichloromethane as eluant) to give 1.49 g of the subtitle compound.

Workup

  1. customAfter a further 1 hour the mixture was partitioned between diethyl ether and water
  2. customThe organic layer was separated
  3. washwashed twice with water
  4. dry with materialThe organic layer was dried (magnesium sulphate)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash column chromatography (using 30% hexane, 70% dichloromethane as eluant)

Sources & evidence

ORD record
ord-eaf0ed6edd5c4b1381feced81db11e0f
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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