Dimethylformamide diethylacetal → Ethyl 3-(dimethylamino)-2-(5-bromopyridin-3-yl)acrylate

HRID 37894

Reaction equation

HRID 37894 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[N:6][CH:7]=1.C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>>[CH3:17][N:18]([CH3:20])[CH:19]=[C:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetate

Product 1

HCID 68799628Ethyl 3-(dimethylamino)-2-(5-bromopyridin-3-yl)acrylate

Procedure

5.1 g (20.9 mmol) of the compound from Example 10A are stirred in 7.2 ml (6.2 g, 41.8 mmol) of dimethylformamide diethyl acetal at a bath temperature of 100° C. for 16 h. After cooling, the mixture is concentrated under reduced pressure, the residue is stirred in diisopropyl ether, and the solid is filtered off and finally washed with diisopropyl ether. The crude product is dried under reduced pressure for 16 h.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated under reduced pressure
  3. filtrationthe solid is filtered off
  4. washfinally washed with diisopropyl ether
  5. dry with materialThe crude product is dried under reduced pressure for 16 h.

Sources & evidence

ORD record
ord-fdad1c24727e4b5282819bcce813ea66
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Linked notes

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