Chlorotriethylsilane → 2-Bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole

HRID 2113290Notes

Reaction equation

HRID 2113290 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([Si:12](Cl)([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].[Br:18][C:19]1[S:23][C:22]2=[C:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[N:25]=[CH:26][N:21]2[C:20]=1[CH2:33][OH:34]>CN(C)C=O.C(OCC)(=O)C>[Br:18][C:19]1[S:23][C:22]2=[C:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[N:25]=[CH:26][N:21]2[C:20]=1[CH2:33][O:34][Si:12]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 13819ChlorotriethylsilaneHCID 81531DiisopropylethylamineHCID 230887952-Bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole

Product 1

HCID 688224232-Bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylethylamine (3.1 ml) and 3.0 ml of triethylsilylchloride were added in that order to a solution of 4.05 g of 2-bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole in 30 ml of dimethylformamide, and the mixture was stirred at room temperature for one hr. The reaction mixture was diluted with ethyl acetate, and the diluted reaction mixture was washed with water, a 5% aqueous sodium bicarbonate solution, and a 20% aqueous sodium chloride solution in that order and was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by column chromatography on silica gel (2 to 5% methanol/methylene chloride) to give 5.14 g of 2-bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole.

Workup

  1. customthe diluted reaction mixture
  2. washwas washed with water
  3. dry with materiala 5% aqueous sodium bicarbonate solution, and a 20% aqueous sodium chloride solution in that order and was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by column chromatography on silica gel (2 to 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-8b14149f2fef478c89ef4acded710dfa
Source dataset
uspto-grants-2009_04
Patent number
US07524951B2

Reaction notes

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