Methyl iodide → 5-Bromo-2-methoxypyridine

HRID 2283456Notes

Reaction equation

HRID 2283456 reaction equation
[CH3:1]I.[Br:3][C:4]1[CH:5]=[CH:6][C:7](=[O:10])[NH:8][CH:9]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:1])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 74%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

Silver carbonate (16.0 g, 57.8 mmol) and methyl iodide (6.5 mL, 103 mmol) were sequentially added to a solution of 5-bromopyridin-2(1H)-one (15.0 g, 86.2 mmol) in benzene (225 mL). The mixture was stirred for 16 h at 50° C. After cooling to room temperature, the mixture was filtered through celite and concentrated. Purification by chromatography using 1-5% ethyl acetate in pet ether provided 12 g of the desired compound: 1H NMR (300 MHz, CDCl3) 8.15-8.25 (narrow m, 1H), 7.63 (dd, J=9, 3 Hz, 1H), 6.63 (d, J=9 Hz, 1H), 3.92 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite and
  3. concentrationconcentrated
  4. customPurification by chromatography

Sources & evidence

ORD record
ord-06cfe2d755b942019db3ba2b1aff63d2
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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