Cyanide → 4-Cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester

HRID 429044노트

반응식

HRID 429044 반응식
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12.[C-:18]#[N:19].[Na+].[C-]#N>CN(C=O)C.C(O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:18]([C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12)#[N:19]

참가 물질

8

반응물 3

HCID 5975CyanideHCID 8929Sodium Cyanide2회HCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

생성물 1

HCID 867575834-Cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester수율 40%

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (10.0 g, 39.5 mmol) in DMF (50 mL) and ethanol (10 mL) was added either sodium cyanide (3.9 g, 80.0 mmol) or tetrabutylarimonium cyanide (11.8 g, 1.1 eq) or tetrabutylammonium chloride (14.7 g, 1.0 eq) and sodium cyanide (2.4 g, 1.2 eq) together. This solution or suspension was warmed up to 60° C. until reaction was completed as judged by TLC. The reaction mixture was then diluted with water (200 mL) and stirred gently at rt for 10 min. A large amount of precipitate formed. The solid was filtered and rinsed thoroughly with water to afford the title compound as an off-white solid after drying: 40-80% yield. This material was >95% pure as judged by HPLC and was used directly without further purification.

후처리

  1. customA large amount of precipitate formed
  2. filtrationThe solid was filtered
  3. washrinsed thoroughly with water

출처 및 근거

ORD 기록
ord-f29d4bde23a8479e8594b6e02fd39747
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316438B1

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