Benzyl Bromide → 3-(Benzyloxy)-6-iodo-2-methylpyridine

HRID 1820953Notes

Reaction equation

HRID 1820953 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH3:1][C:2]1[C:7]([O:8][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 121942112-Methyl-3-hydroxy-6-iodopyridine

Product 1

HCID 735548343-(Benzyloxy)-6-iodo-2-methylpyridineYield 91.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

A suspension of 810 mg (3.45 mmol) of 2-methyl-3-hydroxy-6-iodopyridine (from Step A), 533 μL (4.48 mmol) of benzyl bromide, 953 mg (6.89 mmol) of potassium carbonate and catalytic amount of tetrabutylammonium iodide in 10 mL of acetone was refluxed for 3 h and cooled to rt. Solid was filtered off through a cake of Celite and washed with EtOAc, and the filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 1:19 v/v EtOAc/hexanes as the eluant afforded 1.03 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.48 (s, 3H), 5.04 (s, 2H), 6.79 (d, J=8.4, 1H), 7.32-7.42 (m, 6H).

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationSolid was filtered off through a cake of Celite
  3. washwashed with EtOAc
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9bbece1d584d4911b8c637b15a0990cb
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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