Dimethylformamide → 7-phenyl-Imidazo[1,2-a]pyridine-3-carboxaldehyde

HRID 1245487Notes

Reaction equation

HRID 1245487 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([C:12]2[CH:17]=[CH:16][N:15]3[CH:18]=[CH:19][N:20]=[C:14]3[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C)[CH:23]=[O:24]>>[C:6]1([C:12]2[CH:17]=[CH:16][N:15]3[C:18]([CH:23]=[O:24])=[CH:19][N:20]=[C:14]3[CH:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychloride3×HCID 130430307-Phenylimidazo[1,2-a]pyridine

Product 1

HCID 219128397-phenyl-Imidazo[1,2-a]pyridine-3-carboxaldehyde

Conditions

Temperature
90 °C

Procedure

An oven dried flask under N2 was charged with 2 ml of N,N-dimethylformamide and phosphorous oxychloride (0.048 ml, 0.52 mmol) was added dropwise. 7-Phenylimidazo[1,2-a]pyridine (1-4, 0.100 g, 0.515 mmol) was added and the reaction was heated to 90° C. After 4 h additional POCl3 (0.048 ml, 0.52 mmol) was added and the reaction was heated overnight. Another sample of POCl3 (0.048 ml, 0.52 mmol) was added and heating was continued. After 4 h more, the reaction was cooled to ambient temperature. The reaction was quenched with saturated aqueous NaHCO3 and extracted 3× with DCM. The extracts were dried over Na2SO4, filtered and concentrated.

Workup

  1. customAn oven dried flask under N2
  2. additionwas added dropwise
  3. temperaturethe reaction was heated overnight
  4. temperatureheating
  5. temperaturethe reaction was cooled to ambient temperature
  6. customThe reaction was quenched with saturated aqueous NaHCO3
  7. extractionextracted 3× with DCM
  8. dry with materialThe extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8cb9c4595bd04bf888c1b149b12054a1
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

Loading…