Diisopropylethylamine → HCID 68993836, compound

HRID 347993Notes

Reaction equation

HRID 347993 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[OH:17])[C:5]1=[O:28])(=[O:3])[CH3:2].F[B-](F)(F)F.[CH3:34][O+](C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[O:17][CH3:34])[C:5]1=[O:28])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)2×HCID 178491324HCID 178491324, compound

Product 1

HCID 68993836HCID 68993836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.0 g (10.5 mmol) 1,5-diacetyl-3-[(3,4-dimethoxy-phenyl)-hydroxy-methylidene]-2-indolinone (Ex. V) are suspended in 100 ml methylene chloride and combined with 3.1 g (21 mmol) trimethyloxonium tetrafluoroborate as well as 7.2 ml Hünig base (ethyldiisopropylamine) at ambient temperature. The solution is stirred for 3 h, then a further 1.55 g trimethyloxonium tetrafluoroborate and 3.5 ml Hünig base are added and the mixture is stirred overnight. After the same amount of reagent has been added again and the mixture has been stirred for a further 5 h, the reaction is washed three times with water, the organic phase is dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue is chromatographed through a silica gel column with methylene chloride/methanol 9:1, the corresponding fractions are combined and concentrated by rotary evaporation.

Workup

  1. customat ambient temperature
  2. stirringthe mixture is stirred overnight
  3. additionAfter the same amount of reagent has been added again
  4. stirringthe mixture has been stirred for a further 5 h
  5. washthe reaction is washed three times with water
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue is chromatographed through a silica gel column with methylene chloride/methanol 9:1
  10. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-bd705597827d4000bf2f43cda4281ea6
Source dataset
uspto-grants-2007_02
Patent number
US07176231B2

Reaction notes

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