Sodium Hydroxide → Imidazo[1,2-A]pyridine-7-carbaldehyde

HRID 2400323Notes

Reaction equation

HRID 2400323 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=12.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 11051824Imidazo[1,2-a]pyridine-7-methanol

Product 1

HCID 11029972Imidazo[1,2-A]pyridine-7-carbaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To imidazo[1,2-a]pyridin-7-yl-methanol (100 mg, 0.7 mmol) suspended in chloroform (5 ml) at room temperature was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane, 0.373 g, 0.9 mmol, 1.3 equiv). This mixture was stirred at room temperature overnight and then dilute sodium hydroxide solution was added and the mixture was stirred for 60 minutes. The mixture was then extracted with dichloromethane and the organic liquors were concentrated in vacuo to furnish imidazo[1,2-a]pyridine-7-carbaldehyde (90 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6): 10.00 (1H, s), 8.67 (1H, d), 8.33 (1H, s), 8.20 (1H, s), 7.86 (1H, d), 7.25 (1H, dd).

Workup

  1. stirringthe mixture was stirred for 60 minutes
  2. extractionThe mixture was then extracted with dichloromethane
  3. concentrationthe organic liquors were concentrated in vacuo

Sources & evidence

ORD record
ord-5dc06697a5624f819158bef6e63a17d6
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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