Sodium hydride → HCID 58100934, compound

HRID 1911252Notes

Reaction equation

HRID 1911252 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.Cl[CH2:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1.[H-].[Na+]>>[CH3:1][Si:2]([CH3:17])([CH3:18])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:9]2[CH2:20][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 140908642-(Chloromethyl)-1,3-thiazoleHCID 66845502ethyl 6-trimethylsilyl-1H-indole-2-carboxylate

Product 1

HCID 58100934HCID 58100934, compoundYield 66.5%

Procedure

This compound was prepared according to a process similar to that described in step 20.2, by reacting 570 mg (2.18 mmol) of ethyl 6-trimethylsilyl-1H-indole-2-carboxylate with 440 mg (3.27 mmol) of 2-(chloromethyl)thiazole in the presence of 0.14 g (3.27 mmol) of sodium hydride (55%). The crude reaction product is then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate, to give 520 mg of the expected product.

Workup

  1. customThis compound was prepared
  2. customThe crude reaction product
  3. customis then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-99b3ffbc26ec428281d2950b948623aa
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

Loading…