Imidazole → Pyridine, 2-bromo-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 2086585Notes

Reaction equation

HRID 2086585 reaction equation
N1C=CN=C1.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][OH:14])[N:8]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl>[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[N:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 11483477Pyridine, 2-bromo-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add imidazole (3.01 g, 44.19 mmol) to a solution of the product from Step 1 (5.54 g, 29.46 mmol) and t-butyldimethylsilyl chloride (4.97 g, 32.99 mmol) in CH2Cl2 (60 ml) at RT and stir overnight. Filter the reaction mixture and concentrate the filtrate. Purify the residue by chromatography to give the desired compound.

Workup

  1. filtrationFilter the reaction mixture
  2. concentrationconcentrate the filtrate
  3. customPurify the residue by chromatography

Sources & evidence

ORD record
ord-f83ae1b18e81451bae99b4b2a547c642
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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