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

HRID 1372471Notes

Reaction equation

HRID 1372471 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.Cl[CH2:10][CH:11]=O>C(O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[CH:4]=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

Conditions

Temperature
85 °C

Procedure

To a solution of the product (480 mg, 2.18 mmol) from Step A in ethanol (12 mL) was added chloroacetaldehyde (50 wt. % in water, 0.336 mL) and the mixture was heated at 85° C. for 3 h. After cooling to room temperature, the solution was concentrated under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic phase was separated, dried (magnesium sulfate) and concentrated in vacuo to yield the product as light-brown solid which was used without further purification. LC/MS 244.8 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f62ae5d5d6eb44ff81bb1d6abc7e2e5f
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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