Acetic Acid → 5-chloro-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 490446

反応式

HRID 490446 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]([CH3:24])[CH:12]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.CC(C)([O-])C.[K+].C(O)(=O)C>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:9]=[C:10]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH3:24])[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 23665647Potassium tert-butoxideHCID 671476445-chloro-3-(5,6-dimethoxy-1-methyl-1H-indol-3-ylethynyl)pyridin-2-ylamine

生成物 1

HCID 468681625-chloro-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine収率 63.6%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

A suspension of 0.44 g of 5-chloro-3-(5,6-dimethoxy-1-methyl-1H-indol-3-ylethynyl)pyridin-2-ylamine and 0.58 g of potassium tert-butoxide in 25 ml of 1-methylpyrrolidin-2-one is heated at a temperature in the region of 70° C. for approximately 4 hours 30 minutes. The mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up with 40 ml of water and the pH of the suspension obtained is brought to approximately 4-5 by adding glacial acetic acid. After agitation for approximately 10 minutes, the solid is filter-dried, washed with three times 5 ml of water and then air-dried. After recrystallization from 160 ml of propan-1-ol, 0.28 g of 5-chloro-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine is obtained in the form of a beige solid, the characteristics of which are as follows:

後処理

  1. concentrationThe mixture is concentrated to dryness under reduced pressure (13 kPa)
  2. customthe pH of the suspension obtained
  3. customthe solid is filter-dried
  4. washwashed with three times 5 ml of water
  5. customair-dried
  6. customAfter recrystallization from 160 ml of propan-1-ol

出典と根拠

ORDレコード
ord-fe508c895b1d46958f6ae767c0b9640b
出典データセット
uspto-grants-2009_05
特許番号
US07528147B2

関連ノート

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