Acetonitrile → N-phenyl-6-(pyrid-3-yl)imidazo[1,2-a]pyridine-2-carboxamide

HRID 1878442Notes

Reaction equation

HRID 1878442 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[N:10]=2)[CH:7]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:14]1([NH:13][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:22]4[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=4)=[CH:7][N:6]3[CH:8]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 247716736-bromo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2×

Product 1

HCID 44137633N-phenyl-6-(pyrid-3-yl)imidazo[1,2-a]pyridine-2-carboxamideYield 48.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

150 mg of 6-bromo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 1), 0.237 g of pyridine-3-boronic acid, 45 mg of tetrakis(triphenylphosphine)palladium, 2 mL of aqueous 2M sodium carbonate solution, 4 mL of acetonitrile and 4 mL of toluene are placed in a microwave tube. The mixture is heated for 20 minutes in a microwave machine set at 150° C., and then cooled and filtered, the insoluble matter being washed with a mixture of methanol and dichloromethane. The combined filtrates are concentrated to dryness under reduced pressure. The residue is concreted with aqueous methanol to give 73 mg of N-phenyl-6-(pyrid-3-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of an off-white solid.

Workup

  1. temperatureThe mixture is heated for 20 minutes in a microwave machine
  2. customset at 150° C.
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe insoluble matter being washed with a mixture of methanol and dichloromethane
  6. concentrationThe combined filtrates are concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4b02cd74bd674f53bf290ff6610a4748
Source dataset
uspto-grants-2012_11
Patent number
US08314109B2

Reaction notes

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