乙醚 → 5-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

HRID 31342

反应方程式

HRID 31342 反应方程式
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22].[NH4+].[Cl-].CC[O:27][CH2:28]C>C1COCC1>[CH3:28][O:27][C:12]1[CH:13]=[CH:14][CH:18]=[CH:19][C:20]=1[Mg:1][Br:2].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10]

参与物

8

反应物 5

HCID 3283乙醚2 次HCID 113582-溴苯甲醚HCID 25517氯化铵HCID 872035-氯靛红HCID 5462224Magnesium

产物 2

HCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-oneHCID 178489560HCID 178489560，化合物

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

This compound is prepared according to the procedure disclosed in WO 95/18105. A solution of 2-methoxyphenylmagnesium bromide is prepared from 16 g of magnesium in 35 ml of ether and from a solution of 124 g of 1-bromo-2-methoxybenzene in 175 ml of ether. This solution is added dropwise under an argon atmosphere to a mixture, cooled beforehand in an ice bath, of 30 g of 5-chloro-1H-indole-2,3-dione in 250 ml of THF and then the mixture is left stirring while allowing the temperature to rise to RT. After stirring for 1 hour at RT, the reaction mixture is slowly poured into saturated NH4Cl solution and the THF is evaporated off under vacuum. The precipitate formed is spin-filtered off and is washed with iso ether. 42 g of the expected product are obtained, which product is used without further purification in the following stage.

后处理

  1. customThis compound is prepared
  2. additionThis solution is added dropwise under an argon atmosphere to a mixture
  3. temperaturecooled
  4. waitthe mixture is left
  5. customto rise to RT
  6. stirringAfter stirring for 1 hour at RT
  7. customthe THF is evaporated off under vacuum
  8. customThe precipitate formed
  9. filtrationis spin-filtered off
  10. washis washed with iso ether

来源与证据

ORD记录
ord-63ed12e504da457c9655396a881f37c0
来源数据集
uspto-grants-2008_09
专利号
US07425566B2

关联笔记

加载中…