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

HRID 490446

반응식

HRID 490446 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
70 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-fe508c895b1d46958f6ae767c0b9640b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528147B2

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