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

HRID 1952205Notes

Reaction equation

HRID 1952205 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

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 6228DimethylformamideSolvent

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 at 130° C. for 10 minutes in a microwave device and then concentrated to dryness. The residue is taken up in 100 ml of water and extracted with two times 70 ml of ethyl acetate. The combined organic phases are washed with a saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The solid is triturated from ethyl acetate, filtered off, washed with ethyl acetate and then with isopropyl ether, and taken up in a mixture of methanol and dichloromethane. The insoluble material 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 two times 70 ml of ethyl acetate
  3. washThe combined organic phases are washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe solid is triturated from ethyl acetate
  7. filtrationfiltered off
  8. washwashed with ethyl acetate
  9. additionwith isopropyl ether, and taken up in a mixture of methanol and dichloromethane
  10. filtrationThe insoluble material is filtered off
  11. washwashed with methanol
  12. concentrationThe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6652e40bcdd14766b2de8b0b10952e3a
Source dataset
uspto-grants-2013_03
Patent number
US08404848B2

Reaction notes

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