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6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide → N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide

HRID 1878475
Notes
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Reaction equation

HRID 1878475 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.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC>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.CN(C=O)C>[C:14]1([NH:13][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([CH:20]=[CH2:21])=[CH:7][N:6]3[CH:8]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 441359396-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamideHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 24771613N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228Dimethylformamide
Solvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.73 g of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide, 209 mg of tetrakis(triphenylphosphine)palladium(0), 587 μL of tributylvinyltin and 17 mL of DMF is heated for 10 minutes at 130° C. in a microwave machine and then concentrated to dryness. The residue is taken up in 100 mL of water and extracted with twice 70 mL of ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The solid is triturated in ethyl acetate, filtered off by suction, washed with ethyl acetate and then with isopropyl ether, and taken up in a mixture of methanol and dichloromethane. The insoluble matter is filtered off and washed with methanol. The filtrate is concentrated to dryness under reduced pressure to give 0.29 g of N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. extractionextracted with twice 70 mL of ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe solid is triturated in ethyl acetate
  7. filtrationfiltered off by suction
  8. washwashed with ethyl acetate
  9. additionwith isopropyl ether, and taken up in a mixture of methanol and dichloromethane
  10. filtrationThe insoluble matter is filtered off
  11. washwashed with methanol
  12. concentrationThe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-52f951e4c456474abbd581674ba0065f
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314109B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes