Isopropyl iodide → Methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate

HRID 577539Notes

Reaction equation

HRID 577539 reaction equation
[Br:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH:13](I)([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:5]([O:8][CH:13]([CH3:15])[CH3:14])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6362Isopropyl iodideHCID 178498592HCID 178498592, compound

Product 1

HCID 86723769Methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 5-bromo-2-hydroxypyridine-4-carboxylate (3.00 g, 12.9 mmol), isopropyl iodide (3.30 g, 19.4 mmol) and Ag2CO3 (4.66 g, 16.8 mmol) in toluene (40 mL) was heated at 100° C. for 2 hours. The solid was filtered through CELITE® and the filtrate was concentrated under vacuum and purified by column chromatography (0-20% ethyl acetate/heptanes) to give methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate (112a, 3.5 g, 99%) as a colorless oil.

Workup

  1. filtrationThe solid was filtered through CELITE®
  2. concentrationthe filtrate was concentrated under vacuum
  3. custompurified by column chromatography (0-20% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-3756b21541054e37bf2286d97908e5b5
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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