Phosphorus oxychloride → ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 429043

반응식

HRID 429043 반응식
C(O[C:4](=O)[C:5](=[CH:11][NH:12][C:13]1[N:17]([CH2:18][CH3:19])[N:16]=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:4]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][N:12]=[C:13]2[N:17]([CH2:18][CH3:19])[N:16]=[CH:15][C:14]=12

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychloride2회HCID 12845080Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

생성물 1

HCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate수율 50%

실험 절차

(1-Ethylpyrazol-5-ylamino)methylenemalonate diethyl ester (10.0 g, 42.6 mmol) was dissolved in phosphorus oxychloride (50 mL). This solution was heated at reflux for 10 h before the phosphorus oxychloride was removed via evaporation under reduced pressure. The resulting brown residue was diluted with EtOH (5 mL) and extracted with hot hexane (200 mL×3). The combined organic layers were evaporated under reduced pressure to afford the title compound as an oil which formed light green needle shaped crystals upon standing at room temperature (5.4 g, 21.3 mmol, 50% yield). This material is identical to the one obtained in Preparation 3 (1H NMR, 13C, MS, and HPLC).

후처리

  1. temperatureThis solution was heated
  2. customwas removed via evaporation under reduced pressure
  3. additionThe resulting brown residue was diluted with EtOH (5 mL)
  4. extractionextracted with hot hexane (200 mL×3)
  5. customThe combined organic layers were evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d8b5e2a91eee41d6b41ec7622938532a
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316438B1

연결된 노트

불러오는 중…