Acetonitrile → N,6-diphenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 645364Notes

Reaction equation

HRID 645364 reaction equation
I[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.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][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:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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 66827Phenylboronic AcidHCID 441359396-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Product 1

HCID 24771612N,6-diphenylimidazo[1,2-a]pyridine-2-carboxamideYield 65.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.391 g of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide, 0.237 g of phenylboronic acid, 45 mg of tetrakis(triphenylphosphine)palladium, 4 ml of 2M aqueous sodium carbonate solution, 6 ml of acetonitrile and 6 ml of toluene are charged to a microwave tube. The mixture is heated for 20 minutes in the microwave device adjusted to 150° C. After cooling, the organic phase is separated, dried and evaporated. The residue is taken up in a mixture of dichloromethane and pentane. The solid is filtered off and then purified by triturating from methanol to give 0.22 g of N,6-diphenylimidazo[1,2-a]pyridine-2-carboxamide in the form of an ecru solid.

Workup

  1. temperatureThe mixture is heated for 20 minutes in the microwave device
  2. customadjusted to 150° C
  3. temperatureAfter cooling
  4. customthe organic phase is separated
  5. customdried
  6. customevaporated
  7. additionThe residue is taken up in a mixture of dichloromethane and pentane
  8. filtrationThe solid is filtered off
  9. custompurified
  10. customby triturating from methanol

Sources & evidence

ORD record
ord-69458188f34f415383042d11ddf828ec
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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