Citraconic Anhydrides → N-(5-bromopyridin-2-yl)-methylmaleimide

HRID 12150

Reaction equation

HRID 12150 reaction equation
[C:1]1(=[O:8])O[C:5](=[O:6])[CH:4]=[C:2]1[CH3:3].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1>C1(C)C=CC=CC=1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]2[C:5](=[O:6])[CH:4]=[C:2]([CH3:3])[C:1]2=[O:8])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 12012Citraconic AnhydridesHCID 706222-Amino-5-bromopyridine

Product 1

HCID 22596423N-(5-bromopyridin-2-yl)-methylmaleimideYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of citraconic anhydride (1.00 mL, 11.1 mmol) and 2-amino-5-bromopyridine (1.93 g, 11.2 mmol) in toluene (60 mL) was heated to reflux overnight. The solution was cooled down, filtered. The filtrate was concentrated in vacuo to give a solid (2.10 g, yield: 71%). MS 267 and 269 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureThe solution was cooled down
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d06354339c1c4248aa2e70c96f4c2652
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Linked notes

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