Imidazole → 2-Bromo-3-((tert-butyldimethylsilyloxy)methyl)pyridine

HRID 1471689Notes

Reaction equation

HRID 1471689 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.N1C=CN=C1.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C.O.CCOC(C)=O>[Br:1][C:2]1[C:7]([CH2:8][O:9][Si:19]([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14761460(2-Bromopyridin-3-yl)methanol

Product 1

HCID 227250932-Bromo-3-((tert-butyldimethylsilyloxy)methyl)pyridineYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (2-bromopyridin-3-yl)methanol (20.0 g, 106.4 mmol, 1 eq.; refer to example 14) and imidazole (14.5 g, 212.8 mmol, 2 eq.) in DMF (50.0 mL) was added TBSCl (19.2 g, 150.7 mmol, 1.2 eq.) at rt. The mixture was stirred at rt for 1 h and diluted with a mixture of water (100 mL) and EtOAc (300 mL). The organic layer was washed with NH4Cl(sat) solution and brine, dried over Na2SO4, concentrated, and purified on silica gel using 10% EtOAc/hexanes as eluent to give 2-bromo-3-((tert-butyldimethylsilyloxy)methyl)pyridine (30.1 g, 94%) as a colorless oil. LRMS (M+H+) m/z 302.0.

Workup

  1. washThe organic layer was washed with NH4Cl(sat) solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel using 10% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-6dcad1ec9b8c4de6a1621fc8886f4eeb
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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