Triethylamine → 4-Bromo-2-((tert-butyldimethylsilyl)oxy)-6-methylpyridine

HRID 1366175Notes

Reaction equation

HRID 1366175 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([OH:9])[CH:3]=1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][Si:14]([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178422452HCID 178422452, compound

Product 1

HCID 590230434-Bromo-2-((tert-butyldimethylsilyl)oxy)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-6-methylpyridin-2-ol (376 mg, 2 mmol) in dry DMF (20 mL) is stirred under N2. TBDMS-Cl (600 mg, 4 mmol) is added, followed by triethylamine (0.97 mL, 7.00 mmol), and the mixture is stirred at rt for 1 h. The solution is poured into ice-water (170 mL) and extracted with diethyl ether (5×50 mL). The combined extracts are dried over Na2SO4 and the solvent is evaporated under reduced pressure. The residue is taken up in pentane (50 mL), dried over Na2SO4 and the solvent evaporated again, to afford the crude title compound as a yellow oil. This is used without further purification.

Workup

  1. extractionextracted with diethyl ether (5×50 mL)
  2. dry with materialThe combined extracts are dried over Na2SO4
  3. customthe solvent is evaporated under reduced pressure
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated again

Sources & evidence

ORD record
ord-4ad3f4bde8b34b9c8ae97d495a4e1bf2
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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