Diethyl Ether → 3,5-Dichloro-3-(2-methoxyphenyl)indolin-2-one

HRID 1358476Notes

Reaction equation

HRID 1358476 reaction equation
[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.[NH4+].[Cl-:24].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:24][C:15]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[O:9][CH3:10])[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([Cl:11])[CH:13]=2)[NH:17][C:16]1=[O:21]

Participants

8

Reactant 5

HCID 3283Diethyl Ether2×HCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Product 2

HCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-oneHCID 178489560HCID 178489560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 AT. After stirring for 1 hour at AT, the reaction mixture is slowly poured onto a saturated NH4Cl solution and the THF is evaporated under vacuum. The precipitate formed is filtered off and is washed with iso ether. 42 g of the expected product are obtained, which product is used as is in the following stage.

Workup

  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. stirringAfter stirring for 1 hour at AT
  6. customthe THF is evaporated under vacuum
  7. customThe precipitate formed
  8. filtrationis filtered off
  9. washis washed with iso ether

Sources & evidence

ORD record
ord-4fb6124f230944098d54b931395e7b7b
Source dataset
uspto-grants-2003_07
Patent number
US06596732B2

Reaction notes

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