Sodium Iodide → HCID 15015388, compound

HRID 1110067Notes

Reaction equation

HRID 1110067 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Cl[CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26].[I-].[Na+]>CN(C=O)C>[CH3:1][C:2]1[N:3]([CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:4]2[C:9]([C:10]=1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 75361Silane, (chloromethyl)trimethyl-HCID 15573859(4-Methoxyphenyl)(2-methyl-1H-indol-3-yl)methanone

Product 1

HCID 15015388HCID 15015388, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 15 g. (0.057 mole) of 2-methyl-3-(4-methoxybenzoyl) indole in 120 ml. of DMF under nitrogen was treated with 1.36 g. (0.057 mole) of sodium hydride at 0° C. The mixture was allowed to warm to room temperature over a period of two hours and then treated with 20 ml. of chloromethyl trimethylsilane and a catalytic amount of sodium iodide and stirred at room temperature for about twelve hours. The solvent was removed by distillation in vacuo, the residue was mixed with 500 ml. of diethyl ether and the mixture filtered. The filtrate was taken to dryness, and the residue was chromatographed on silica gel, eluting with 30% ethyl acetate/hexane. The product, consisting of 16.5 g. of 2-methyl-3-(4-methoxybenzoyl)-1-trimethylsilylmethyl-1H-indole, was isolated as a light amber oil from the initial, more mobile fractions.

Workup

  1. customat 0° C
  2. additiontreated with 20 ml
  3. customThe solvent was removed by distillation in vacuo
  4. additionthe residue was mixed with 500 ml
  5. filtrationof diethyl ether and the mixture filtered
  6. customthe residue was chromatographed on silica gel
  7. washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d222a6bf0ea44381b7f771c2e944da24
Source dataset
uspto-grants-1994_06
Patent number
US05324737

Reaction notes

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