5-Bromopyridine-2,3-diamine → 6-Bromoimidazo[1,2-a]pyridin-8-amine

HRID 1969108Notes

Reaction equation

HRID 1969108 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.Cl[CH2:11][CH:12]=O.O>CC(O)C>[Br:9][C:5]1[CH:6]=[C:7]([NH2:8])[C:2]2[N:3]([CH:11]=[CH:12][N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 6911565-Bromopyridine-2,3-diamineHCID 12227820Acetaldehyde, chloro-, hydrate

Product 1

HCID 177503946-Bromoimidazo[1,2-a]pyridin-8-amineYield 93.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,3-diamino-5-bromopyridine (10.0 g, 45.86 mmol) was dissolved in 80 ml of IPA and then 50% wt chloroacetaldehyde/H2O (6.51 ml, 50.45 mmol) was added. The resulting mixture was heated at reflux for 24 hrs. The mixture was cooled down and then filtered. The cake was dried to afford 9.10 g of product.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 24 hrs
  3. temperatureThe mixture was cooled down
  4. filtrationfiltered
  5. customThe cake was dried

Sources & evidence

ORD record
ord-925180d0a90949ccb110155ab3ccb8b7
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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