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

HRID 429043

反応式

HRID 429043 の反応式
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

参加物

3

反応物 2

HCID 24813Phosphorus oxychloride2 回HCID 12845080Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

生成物 1

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

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-d8b5e2a91eee41d6b41ec7622938532a
出典データセット
uspto-grants-2001_11
特許番号
US06316438B1

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