Pyridine → Imidazo(1,2-a)pyridine-3-carbonitrile, 2-methyl-

HRID 2282209ノート

反応式

HRID 2282209 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11]([NH2:13])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11]#[N:13]

参加物

6

反応物 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 89061Imidazo(1,2-a)pyridine-3-carboxamide, 2-methyl-HCID 516892Sodium Bicarbonate

生成物 1

HCID 88232Imidazo(1,2-a)pyridine-3-carbonitrile, 2-methyl-収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 2-methylimidazo[1,2-a]pyridine-3-carboxamide (3.50 g, 20 mmol) produced above, pyridine (4.85 mL, 60 mmol) and tetrahydrofuran (50 mL) was added dropwise a solution of trifluoroacetic anhydride (4.24 mL, 30 mmol) in tetrahydrofuran (10 mL) under ice-cooling. The mixture was stirred at room temperature for 1 hr, saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with ethyl acetate/diisopropyl ether to give the title compound (2.5 g, 80%) as a pale-brown solid.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe collected organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe insoluble material was filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washthe obtained residue was washed with ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-b42b83ae79a942d0a5acaac369f8518e
出典データセット
uspto-grants-2015_09
特許番号
US09139589B2

反応ノート

読み込み中…