Tetrahydrofuran → 2,4-dibromo-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thiazole

HRID 2402066Notes

Reaction equation

HRID 2402066 reaction equation
[H-].[Na+].O1CCCC1.[Br:8][C:9]1[S:10][C:11]([C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)=[C:12]([Br:14])[N:13]=1.[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl>>[Br:8][C:9]1[S:10][C:11]([C:15]2[N:19]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:28])([CH3:27])[CH3:20])[CH:18]=[CH:17][N:16]=2)=[C:12]([Br:14])[N:13]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 580948752,4-dibromo-5-(1H-imidazol-2-yl)thiazole

Product 1

HCID 580947602,4-dibromo-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thiazoleYield 81.7%

Procedure

To a mixture of sodium hydride (2.89 g, 72.2 mmol) in tetrahydrofuran (431 mL, 5310 mmol) was added 2,4-dibromo-5-(1H-imidazol-2-yl)thiazole (18.81 g, 60.88 mmol) in tetrahydrofuran (60 mL, 700 mmol) at 0° C. The mixture was stirred for 30 min before [β-(Trimethylsilyl)ethoxy]methyl chloride (11.85 mL, 66.96 mmol) in tetrahydrofuran (24 mL, 3.0E2 mmol) was added slowly at 0° C. The reaction was quenched with MeOH. The solvent was evaporated and the residue was purified by column chromatography on silica gel to afford 2,4-dibromo-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thiazole (13.6 g, 81.7%). LCMS (AA) ES+ 440, 442.

Workup

  1. additionwas added slowly at 0° C
  2. customThe reaction was quenched with MeOH
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ee9a20af3d424549a2e3d3332b105681
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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