Chloroacetaldehyde → 6-Bromoimidazo[1,2-a]pyridine

HRID 2037839Notes

Reaction equation

HRID 2037839 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Cl[CH2:10][CH:11]=O>C(O)C.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 706222-Amino-5-bromopyridine

Product 1

HCID 27955476-Bromoimidazo[1,2-a]pyridineYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.00 g of 2-amino-5-bromopyridine (3) is dissolved in ethanol (35 mL), and chloroacetaldehyde in water (2.52 mL, 6.1 mol/L) was added and the reaction mixture was heated at reflux for 3 hours. The reaction mixture was concentrated, and saturated aqueous NaHCO3 was added to the residue, and it is extracted with ethyl acetate. After conventional workup afford 2.30 g of the titled compound as a brown powder (yield: 100%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionsaturated aqueous NaHCO3 was added to the residue, and it
  5. extractionis extracted with ethyl acetate

Sources & evidence

ORD record
ord-9722495747a14a6fa715cdf237909b68
Source dataset
uspto-grants-2013_11
Patent number
US08575337B2

Reaction notes

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