Phosphorus oxychloride → 5-Chloro-1H-pyrrolo(3,2-b)pyridine
反応式
[N:1]1[CH:2]=[CH:3][C:4]2[C:9]=1[CH:8]=[CH:7][C:6](=O)[N:5]=2.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:6]1[N:5]=[C:4]2[CH:3]=[CH:2][NH:1][C:9]2=[CH:8][CH:7]=1参加物
3
実験手順
A mixture of pyrrolo[3,2-b]pyrid-5-one (prepared according to the procedure described in J. Med. Chem. 1990, 33, 2087) (1.33 g, 9.91 mmol) and 20 mL of phosphorous oxychloride is heated in a sealed Parr high pressure stainless steel vessel at 180° C. for 2.5 hours. After cooling, excess phosphorous oxychloride is removed in vacuo. The residue is cooled in an ice bath and quenched with ice water. The resulting mixture is neutralized by addition of saturated NaHCO3 solution and extracted with EtOAc (3×). The combined organic layers are dried over MgSO4, filtered and concentrated in vacuo. The crude product (1.07 g, 7.01 mmol) is used in the subsequent step without further purification.
後処理
- customprepared
- temperatureAfter cooling
- customexcess phosphorous oxychloride is removed in vacuo
- temperatureThe residue is cooled in an ice bath
- customquenched with ice water
- additionThe resulting mixture is neutralized by addition of saturated NaHCO3 solution
- extractionextracted with EtOAc (3×)
- dry with materialThe combined organic layers are dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
出典と根拠
- ORDレコード
- ord-95cd96aa7b094e93a2ec8b0dbb5eb4c8
- 出典データセット
- uspto-grants-2001_08
- 特許番号
- US06281227B1
反応ノート
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