Tetrahydrofuran → HCID 5297649, compound

HRID 1581702Notes

Reaction equation

HRID 1581702 reaction equation
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[CH3:11][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-].C1[CH2:29][O:28]CC1>>[CH3:29][O:28][C:12]1[CH:13]=[CH:14][CH:18]=[CH:19][C:20]=1[Mg:1][Br:2].[CH3:11][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]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran3×HCID 113582-BromoanisoleHCID 118405-MethylisatinHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 2

HCID 5297649HCID 5297649, compoundHCID 178489560HCID 178489560, compound

Procedure

A solution of 2-methoxyphenylmagnesium bromide is prepared from 6.8 g of magnesium in 15 ml of THF and from a solution of 52.5 g of 1-bromo-2-methoxybenzene in 75 ml of THF. This solution is added dropwise at RT, under an argon atmosphere, to a mixture of 8.9 g of 5-methyl-1H-indole-2,3-dione in 80 ml of THF and is then refluxed for 3 hours. After cooling to RT, saturated NH4Cl solution is added to the reaction mixture, the resulting mixture is extracted three times with EtOAc and the combined organic phases are washed twice with water and with saturated NaCl solution, dried over Na2SO4 and the solvent is partially concentrated. The precipitate formed is spin-filtered off to give 9 g of the expected product.

Workup

  1. temperatureis then refluxed for 3 hours
  2. extractionthe resulting mixture is extracted three times with EtOAc
  3. washthe combined organic phases are washed twice with water and with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationthe solvent is partially concentrated
  6. customThe precipitate formed
  7. filtrationis spin-filtered off

Sources & evidence

ORD record
ord-8f33cfb8e4d240f0a36aea5668bf43e7
Source dataset
uspto-grants-2004_05
Patent number
US06730695B2

Reaction notes

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