Methyl iodide → 6-Methoxy-3,3-dimethylindolin-2-one

HRID 892201노트

반응식

HRID 892201 반응식
[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.[CH3:14]N(CCN(C)C)C.[Li]CCCC.IC>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 222415386-Methoxy-3-methyl-1,3-dihydro-indol-2-oneHCID 178418339Butyllithium

생성물 1

HCID 222416036-Methoxy-3,3-dimethylindolin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-25 °C

실험 절차

To a cooled solution (−78° C.) of 6-methoxy-3-methyl-1,3-dihydro-indol-2-one (679 mg, 3.83 mmol, example 77) in THF (13 mL) is added TMEDA (1.16 mL, 7.66 mmol) followed by dropwise addition of 2.5M n-BuLi (3.06 mL, 7.66 mmol). The mixture is stirred 15 min then warmed to −25° C. Iodomethane (275 μL, 4.40 mmol) is added dropwise and stirred for 30 min. 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, 35% ethyl acetate in hexanes) to give the title compound as a white crystalline solid. MS (ESI) 192 (M+H)+.

후처리

  1. stirringstirred for 30 min
  2. customReaction
  3. customis quenched with sat NH4Cl soln
  4. temperaturewarmed to room temp
  5. additiondiluted with EtOAc
  6. dry with materialWashed organic layer with sat NH4Cl soln, brine, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (silica, 35% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-d257a4a7c4b94205a56784f4e7b3df6e
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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