Methyl iodide → 3-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 1829010Notes

Reaction equation

HRID 1829010 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2.[CH:21]([N:24]([CH2:28]C)[CH:25]([CH3:27])[CH3:26])(C)C.I[CH3:31].[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[CH3:21][N:24]([CH3:28])[C:25]1[CH:27]=[C:33]2[C:32](=[CH:31][CH:26]=1)[C:36](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:35][CH2:34]2.[CH3:21][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 696596273-(5-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 2

HCID 688381003-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-oneHCID 69659582HCID 69659582, compound

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

To a solution of 3-(5-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol) and N,N-diisopropylethylamine (65.8 μL, 0.378 mmol) in 2.0 mL THF was added iodomethane (12.9 μL, 0.208 mmol). After stirring at room temperature for 21 h, silver triflate (53.4 mg, 0.208 mmol) was added and the mixture heated at 45° C. for 16 h. The mixture was partitioned between EtOAc and saturated NaHCO3 and the organic separated. The organic layer was washed with H2O, brine and then dried with Na2SO4. The solution was evaporated in vacuo and chromatographed with 2% MeOH/CHCl3 to give 3-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (1.2 mg) as a yellow-orange solid and 3-(5-Methylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (8.9 mg) as an orange solid.

Workup

  1. temperaturethe mixture heated at 45° C. for 16 h
  2. customThe mixture was partitioned between EtOAc and saturated NaHCO3
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. customThe solution was evaporated in vacuo
  6. customchromatographed with 2% MeOH/CHCl3

Sources & evidence

ORD record
ord-dc77757ad431495dad07e700182e8c59
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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