Aniline → 6-isopropyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 645372Notes

Reaction equation

HRID 645372 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]([O:15]CC)=O)[N:12]=2)[CH:9]=1)([CH3:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.ON1C2N=CC=CC=2N=N1>C1(C)C=CC=CC=1.CC(C)([O-])C.[Zr+4].CC(C)([O-])C.CC(C)([O-])C.CC(C)([O-])C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:15])[N:12]=2)[CH:9]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6115AnilineHCID 181649HOAtHCID 68682228Ethyl 6-isopropylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 686148456-isopropyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamideYield 15.2%

Reagents, catalysts & solvents 2

HCID 10221590Zirconium(IV) tert-butoxideCatalystHCID 1140TolueneSolvent

Procedure

A solution of 344 mg of ethyl 6-isopropylimidazo[1,2-a]pyridine-2-carboxylate, 152 mg of aniline, 40 mg of 1-hydroxy-7-azabenzotriazole (HOAt) and 316 mg of zirconium tert-butoxide in 5 ml of toluene is stirred at ambient temperature for 16 hours in a microwave tube. The medium is concentrated to dryness under reduced pressure and the residue is chromatographed on a silica cartridge, elution being carried out with a mixture of dichloromethane and ethyl acetate (50/50). The fractions comprising the expected product are combined and concentrated to dryness under reduced pressure to give 63 mg of 6-isopropyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. concentrationThe medium is concentrated to dryness under reduced pressure
  2. customthe residue is chromatographed on a silica cartridge, elution
  3. additionbeing carried out with a mixture of dichloromethane and ethyl acetate (50/50)
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c1bb3b99e3534ab68099dab4a3fa8b3b
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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