Methyl iodide → 3-Bromo-2-chloro-5-methoxypyridine

HRID 1621389Notes

Reaction equation

HRID 1621389 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].CI.[Br:9][C:10]1[CH:11]=[C:12](O)[CH:13]=[N:14][C:15]=1[Cl:16]>CN(C=O)C.O>[Br:9][C:10]1[C:15]([Cl:16])=[N:14][CH:13]=[C:12]([O:4][CH3:1])[CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 145952265-Bromo-6-chloropyridin-3-ol

Product 1

HCID 467388143-Bromo-2-chloro-5-methoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

K2CO3 (0.50 g, 3.6 mmol) followed by methyl iodide (0.20 mL, 2.9 mmol) were added to a stirred mixture of 5-bromo-6-chloropyridin-3-ol (Asymchem Laboratories, Inc., Morrisville, N.C.) (0.50 g, 2.4 mmol) in DMF (3.00 mL) and the mixture was sealed and heated at 45° C. for 4 h and then allowed to stand at room temperature overnight. The resulting mixture was diluted with water and the precipitate was collected and dried to give the product as a tan solid. LCMS (API-ES) m/z 223 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H) 7.49 (d, J=1.37 Hz, 1H) 3.86 (s, 3H).

Workup

  1. customthe mixture was sealed
  2. customthe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-bee9a5cbb70c4468bdeaa1d6dda788ab
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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