Imidazole → 4-Bromo-2-[(t-butyldimethylsilyloxy)methyl]-5-methylpyridine

HRID 2080478Notes

Reaction equation

HRID 2080478 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].ClCCl.[Br:17][C:18]1[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([CH2:25][OH:26])[CH:19]=1>CN(C)C1C=CN=CC=1.CCCCCC.O>[Br:17][C:18]1[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([CH2:25][O:26][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11])[CH:19]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 23114663(4-Bromo-5-methylpyridin-2-yl)methanol

Product 1

HCID 231148234-Bromo-2-[(t-butyldimethylsilyloxy)methyl]-5-methylpyridineYield 100%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, imidazole (2.95 g, 43.3 mmol), 4-dimethylaminopyridine (481 mg, 3.94 mmol) and t-butylchlorodimethylsilane (6.53 g, 43.3 mmol) were added to a dichloromethane solution (100 ml) of (4-bromo-5-methylpyridin-2-yl)methanol (7.96 g, 39.4 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure to give the title compound (12.4 g, 39.4 mmol, quant.) as a pale yellow oil.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. concentrationethyl acetate=4:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6c9d3f18b78d4c9aba0f7fdf19d524b8
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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