Pyridine → E 7820

HRID 2355781

反応式

HRID 2355781 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]#[N:12].N1C=CC=CC=1.[C:20]([C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1)#[N:21]>O1CCCC1>[C:11]([C:7]1[C:6]2[C:10](=[C:2]([NH:1][S:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:20]#[N:21])[CH:23]=3)(=[O:30])=[O:29])[CH:3]=[CH:4][C:5]=2[CH3:13])[NH:9][CH:8]=1)#[N:12]

参加物

5

反応物 3

HCID 1049PyridineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 117152477-amino-4-methyl-1H-indole-3-carbonitrile

生成物 1

HCID 196970E 7820収率 47.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7-amino-3-cyano-4-methyl-1H-indole (10 g, 58.4 mmol) in tetrahydrofuran (200 ml) were added pyridine (20 ml) and 3-cyanobenzenesulfonyl chloride (12.5 g), followed by stirring at room temperature for 3.5 hours. After further adding 2N hydrochloric acid (100 ml), extraction was performed with ethyl acetate. The organic layer was washed with water (twice) and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-3:2). A mixed solvent of ethanol-hexane (1:2) was added thereto, and after sonication, the precipitate was collected by filtration and washed with a mixed solvent of ethanol-hexane (1:3). The mixture was dried overnight under reduced pressure to give the title compound (9.33 g, 27.7 mmol, 47% yield).

後処理

  1. additionAfter further adding
  2. extraction2N hydrochloric acid (100 ml), extraction
  3. washThe organic layer was washed with water (twice) and brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-3:2)
  7. additionA mixed solvent of ethanol-hexane (1:2) was added
  8. customafter sonication
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with a mixed solvent of ethanol-hexane (1:3)
  11. customThe mixture was dried overnight under reduced pressure

出典と根拠

ORDレコード
ord-a1376e18842647db882858a5a7bf7bda
出典データセット
uspto-grants-2010_07
特許番号
US07754894B2

関連ノート

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