Tetrahydrofuran → HCID 5297649, compound

HRID 1593395Notes

Reaction equation

HRID 1593395 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 drop wise 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. additionThis solution is added drop wise at RT
  2. temperatureis then refluxed for 3 hours
  3. extractionthe resulting mixture is extracted three times with EtOAc
  4. washthe combined organic phases are washed twice with water and with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationthe solvent is partially concentrated
  7. customThe precipitate formed
  8. filtrationis spin-filtered off

Sources & evidence

ORD record
ord-4f76ce24952c4aea997c1354b82cb486
Source dataset
uspto-grants-2007_11
Patent number
US07297692B2

Reaction notes

Loading…