Chloroacetaldehyde → 6-Iodoimidazo(1,2-a)pyridine

HRID 383306Notes

Reaction equation

HRID 383306 reaction equation
Cl[CH2:2][CH:3]=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][N:7]=1>C(O)C>[I:12][C:9]1[CH:10]=[CH:11][C:6]2[N:7]([CH:2]=[CH:3][N:5]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 27643276-Iodoimidazo(1,2-a)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 50% aq. chloroacetaldehyde (1.5 eq, 125 mmol, 16 ml) in ethanol (625 ml) is added 2-amino-5-iodo-pyridine (1 eq, 113 mmol, 25 g) at room temperature. The reaction mixture is heated at reflux for 18 hours. The solvent is removed in vacuo and the crude product is dissolved in water (400 ml). The aqueous solution is treated with sodium bicarbonate to pH=8 and extracted with DCM (3×250 ml). The organic portion is dried (MgSO4) and evaporated to give a beige solid of the title compound. 1H nmr (CDCl3) 8.44 (1H, s), 7.60 (1H, s), 7.53 (1H, s), 7.42 (1H, d, J=9.4 Hz), and 7.33 (1H, d, J=9.58 Hz).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent is removed in vacuo
  4. dissolutionthe crude product is dissolved in water (400 ml)
  5. additionThe aqueous solution is treated with sodium bicarbonate to pH=8
  6. extractionextracted with DCM (3×250 ml)
  7. dry with materialThe organic portion is dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-5aa360f2dc1445b8ab13b0c45c012933
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

Loading…