Dimethylformamide → 7-Methoxyimidazo(1,2-a)pyridine-3-carbaldehyde

HRID 273318Notes

Reaction equation

HRID 273318 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1.O=P(Cl)(Cl)Cl.CN(C)[CH:19]=[O:20]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([CH:19]=[O:20])=[CH:10][N:11]=[C:5]2[CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 450881887-Methoxyimidazo[1,2-a]pyridine

Product 1

HCID 529516207-Methoxyimidazo(1,2-a)pyridine-3-carbaldehydeYield 69%

Conditions

Temperature
90 °C

Procedure

7-Methoxyimidazo[1,2-a]pyridine (621 mg, 4.2 mmol) was mixed with POCl3 (16.8 mmol) in dimethylformamide (4 mL). The reaction mixture was heated at 90° C. for 24 h and then cooled to room temperature. After the solvent was removed in vacuo, an oil was obtained. The oil was purified on a silica gel column eluting with EtOAc/Hexane (1:1) to afford 7-methoxyimidazo[1,2-a]pyridine-3-carbaldehyde (508 mg, 69%).

Workup

  1. temperaturecooled to room temperature
  2. customAfter the solvent was removed in vacuo
  3. customan oil was obtained
  4. customThe oil was purified on a silica gel column
  5. washeluting with EtOAc/Hexane (1:1)

Sources & evidence

ORD record
ord-09db8c1965d74d4cb830194e77de078e
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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