Tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)acrylate → Tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)propanoate

HRID 70554Notes

Reaction equation

HRID 70554 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pt]>[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 86658007Tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58452887Tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)propanoateYield 90%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% platinum-activated carbon was added to a solution of tert-butyl 3-(6-bromo-2-methoxypyridin-3-yl)acrylate (727 mg) in ethyl acetate (7.3 mL), and the mixture was stirred for four hours in a hydrogen atmosphere. The reaction solution was filtered through celite and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the title compound as a colorless oil (657 mg, 90%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-4fe6d62e951d48ad984040105fe6b889
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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