Phosphorus oxychloride → Ethyl 5-amino-2,6-dichloroimidazo[1,2-a]pyridine-8-carboxylate

HRID 1168265Notes

Reaction equation

HRID 1168265 reaction equation
[NH2:1][C:2]1[N:7]2[CH2:8][C:9](=O)[N:10]=[C:6]2[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[Cl:17].P(Cl)(Cl)([Cl:20])=O>>[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([Cl:20])[N:10]=[C:6]2[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[Cl:17]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468963HCID 178468963, compound

Product 1

HCID 22992207Ethyl 5-amino-2,6-dichloroimidazo[1,2-a]pyridine-8-carboxylateYield 72%

Procedure

A solution of ethyl 5-Amino-6-chloro-2-oxo-2,3-dihydroimidazo[1,2-a]pyridine-8-carboxylate (EXAMPLE 24, Step 2, 0.50 g, 2.00 mmol) in phosphorus oxychloride (4 mL) was refluxed for 4 h. After cooling, the mixture was evaporated. The obtained residue was carefully treated with water and 25% aqueous ammonia. The formed solid was collected by filtration to give 385 mg (72%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated
  3. additionThe obtained residue was carefully treated with water and 25% aqueous ammonia
  4. filtrationThe formed solid was collected by filtration

Sources & evidence

ORD record
ord-1a51253f8d68421796c2a85f4d4e2826
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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