Cyclopropanecarboxaldehyde → HCID 53629179, compound

HRID 1896443Notes

Reaction equation

HRID 1896443 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[Br:6][C:7]1[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[N:11][CH:12]=1>CC(O)=O.O1CCOCC1>[Br:6][C:7]1[CH:8]=[C:9]2[NH:14][C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:13][C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 53629179HCID 53629179, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of cyclopropanecarbaldehyde (0.89 g, 12.76 mmol, 1.2 eq), 5-bromopyridine-2,3-diamine x167 (2 g, 10.63 mmol, 1 eq) in AcOH (20 ml) and 1,4-dioxane (40 ml) is heated at 110° C. during 24 hours. After cooling, the solvents are evaporated under reduced pressure. The resulting brown solid is recrystallized in CH2Cl2/hexane (1/1) to yield 0.53 g of 6-bromo-2-cyclopropyl-1H-imidazo[4,5-b]pyridine x168 as an orange solid.

Workup

  1. temperatureAfter cooling
  2. customthe solvents are evaporated under reduced pressure
  3. customThe resulting brown solid is recrystallized in CH2Cl2/hexane (1/1)

Sources & evidence

ORD record
ord-79fef82dfaf24a55b875ce8fa1e4d9b4
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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