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

HRID 645365ノート

反応式

HRID 645365 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4f79e5aba68c425db7a6b72693c8c400
出典データセット
uspto-grants-2010_04
特許番号
US07704989B2

反応ノート

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