Dimethylformamide → 8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridine-3-carbaldehyde

HRID 1295875Notes

Reaction equation

HRID 1295875 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[Cl:11][C:12]1[C:13]2[N:14]([CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[N:20]=2)[CH:15]=[CH:16][CH:17]=1>O>[Cl:11][C:12]1[C:13]2[N:14]([C:18]([CH:3]=[O:4])=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[N:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 113689278-Chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyridine

Product 1

HCID 878860048-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridine-3-carbaldehydeYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-Dimethylformamide (30 mL) was cooled to 0° C. and treated with phosphorous oxychloride (1.08 mL, 11.6 mmol). After the addition was complete, the mixture was warmed to room temperature and stirred for 10 minutes. To this was added 8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridine (2.0 g, 7.75 mmol) and the resulting solution was stirred for 48 hours. Water was added to the reaction. The solids were then filtered and azeoptroped with methanol to give 8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridine-3-carbaldehyde (2.2 g, 99%) as a white solid.

Workup

  1. additionAfter the addition
  2. stirringthe resulting solution was stirred for 48 hours
  3. filtrationThe solids were then filtered

Sources & evidence

ORD record
ord-ba6f3d7ec6fc4c169be6b519d176d2ab
Source dataset
uspto-grants-2007_07
Patent number
US07244740B2

Reaction notes

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