Methyl iodide → HCID 69659266, compound

HRID 1263727Notes

Reaction equation

HRID 1263727 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.[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:32]2[C:33]([CH2:34][O:35][C:36]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:31][CH:26]=1.[CH3:21][NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 2

HCID 69659266HCID 69659266, compoundHCID 69659761HCID 69659761, compound

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

To a solution of 3-(6-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 the residue purified by chromatography (silica gel, 2% MeOH/CHCl3) to give 3-(6-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (3.6 mg) as a yellow solid and 3-(6-Methylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (6.3 mg) as a yellow 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. customthe residue purified by chromatography (silica gel, 2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-b2038ba7c3884d1682805462375e3104
Source dataset
uspto-grants-2003_04
Patent number
US06541504B1

Reaction notes

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