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

HRID 1263728Notes

Reaction equation

HRID 1263728 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 696595823-(5-Methylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

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-2c3d74e420ae4c6d90af1d347a884f42
Source dataset
uspto-grants-2003_04
Patent number
US06541504B1

Reaction notes

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