Dimethylformamide → 6-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde

HRID 219102Notes

Reaction equation

HRID 219102 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[CH:11]1[C:19]([Br:20])=[CH:18][N:17]2[C:13](=[N:14][CH:15]=[CH:16]2)[CH:12]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>>[CH:11]1[C:19]([Br:20])=[CH:18][N:17]2[C:13](=[N:14][CH:15]=[C:16]2[CH:4]=[O:5])[CH:12]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 27955476-Bromoimidazo[1,2-a]pyridine

Product 1

HCID 213456766-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde

Conditions

Temperature
0 °C

Procedure

A 250 mL RB flask was charged with DMF (21.3 ml, 274 mmol) and cooled to 0° C.; phosphorus oxychloride (2.46 ml, 26.4 mmol) was added dropwise. This was stirred for 1 hour, then 6-bromoH-imidazo[1,2-a]pyridine (2.00 g, 10.2 mmol) was added in one portion. This was stirred at 100° C. for 5 hours and at room temperature for 16 hours. The flask was cooled to 0° C. and slowly neutralized with 6N aq. NaOH and sat. aq. NaHCO3, resulting in the formation of a precipitate which was collected by filtration to give 6-bromoH-imidazo[1,2-a]pyridine-3-carbaldehyde as a yellow-orange solid.

Workup

  1. stirringThis was stirred at 100° C. for 5 hours and at room temperature for 16 hours
  2. customresulting in the formation of a precipitate which
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-9a8216343948490cb700ea5c96427462
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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