Imidazole → 5-Bromo-2-((triisopropylsilyloxy)methyl)thiazole

HRID 1520459Notes

Reaction equation

HRID 1520459 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][OH:8])=[N:4][CH:3]=1.N1C=CN=C1.CN(C)C=O.Cl[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>C(OC(=O)C)C>[Br:1][C:2]1[S:6][C:5]([CH2:7][O:8][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 139400Triisopropylsilyl chlorideHCID 11953783(5-Bromo-1,3-thiazol-2-yl)methanol

Product 1

HCID 866954185-Bromo-2-((triisopropylsilyloxy)methyl)thiazoleYield 104%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 100 mL round bottom flask is charged with (5-bromothiazol-2-yl)methanol (2.5 g, 12.9 mmol), imidazole (1.75 g, 25.8 mmol), dimethylformamide (25 mL), and chlorotriisopropylsilane (3.4 mL, 15.5 mmol). The reaction is stirred at room temperature under nitrogen for 72 hours. Contents are diluted with ethylacetate (150 mL), washed with 0.5M hydrochloric acid (2×100 mL) and brine (100 mL), dried (Na2SO4), and concentrated under vacuum to afford the title compound (4.7 g): m/z (Cl) M+H 350+352.

Workup

  1. washwashed with 0.5M hydrochloric acid (2×100 mL) and brine (100 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-322c10200cfb47ac918a6533d8cb31db
Source dataset
uspto-grants-2015_07
Patent number
US09073894B2

Reaction notes

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