Dimethylformamide → 8-(Phenylmethoxy)imidazo[1,2-a]pyridine-3-carboxaldehyde

HRID 2210407Notes

Reaction equation

HRID 2210407 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([CH:15]=[CH:16][N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)Cl.[OH-].[Na+].CN([CH:28]=[O:29])C>>[CH:28]([C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:10]2=[N:17][CH:16]=1)=[O:29]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 134329748-(Benzyloxy)imidazo[1,2-a]pyridine

Product 1

HCID 136802028-(Phenylmethoxy)imidazo[1,2-a]pyridine-3-carboxaldehyde

Conditions

Temperature
10 °C

Procedure

A mixture of 10 g of 8-(phenylmethoxy)imidazo[1,2-a]pyridine prepared in Example 13 and 31 ml of DMF is cooled to 10° C. 4.7 ml of POCl3 are added dropwise. The mixture is allowed to return to room temperature and then heated at 100° C. for 30 min. After cooling, 85 ml of H20 and 16 ml of NaOH (50%) are added. The mixture is heated at 90° C. for 1 h and then allowed to cool. The solid obtained is filtered off and then washed with water until the pH of the mother liquors is neutral. This gives 8.8 g of 3-formyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine.

Workup

  1. customto return to room temperature
  2. temperatureheated at 100° C. for 30 min
  3. temperatureAfter cooling
  4. temperatureThe mixture is heated at 90° C. for 1 h
  5. temperatureto cool
  6. customThe solid obtained
  7. filtrationis filtered off
  8. washwashed with water until the pH of the mother liquors

Sources & evidence

ORD record
ord-576445d392e14d4096421a57126ee04a
Source dataset
uspto-grants-1995_10
Patent number
US05459132

Reaction notes

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