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

HRID 1263728노트

반응식

HRID 1263728 반응식
[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

참가 물질

7

반응물 4

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

생성물 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

시약·촉매·용매 1

HCID 76223Silver(I) trifluoromethanesulfonate촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2c3d74e420ae4c6d90af1d347a884f42
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541504B1

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