Methyl iodide → 6-Methoxy-3-methyl-1,3-dihydro-indol-2-one

HRID 892200ノート

反応式

HRID 892200 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[CH3:13]N(CCN(C)C)C.[Li]CCCC.IC>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 27937496-MethoxyoxindoleHCID 178418339Butyllithium

生成物 1

HCID 222415386-Methoxy-3-methyl-1,3-dihydro-indol-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-25 °C

実験手順

To a cooled solution (−78° C.) of 6-methoxy-1,3-dihydro-indol-2-one (840 mg, 5.2 mmol, See Quallich, Synthesis 1993, 51–53) in THF (20 mL) is added dropwise TMEDA (1.57 mL, 10.4 mL) followed by dropwise addition of 2.5M n-BuLi (4.16 mL, 10.4 mmol). The mixture is allowed to stir for 15 min then warmed to −25° C. Iodomethane (405 μL, 6.5 mmol) is added dropwise and stirred for 20 min. The reaction is quenched with sat NH4Cl soln, warmed to room temp and diluted with EtOAc. Washed organic layer with sat NH4Cl soln, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 45% ethyl acetate in hexanes) to give the title compound. MS (ESI) 178 (M+H)+.

後処理

  1. stirringstirred for 20 min
  2. customThe reaction is quenched with sat NH4Cl soln
  3. temperaturewarmed to room temp
  4. additiondiluted with EtOAc
  5. dry with materialWashed organic layer with sat NH4Cl soln, brine, dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography (silica, 45% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-6ba04cfbd46848469ec248f0df1d7b56
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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