Methyl iodide → Methyl 1-methyl-1H-indole-3-carboxylate

HRID 18224노트

반응식

HRID 18224 반응식
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1.[CH3:16]I>CN(C=O)C.O>[CH3:16][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2회HCID 589098Methyl indole-3-carboxylate

생성물 1

HCID 842006Methyl 1-methyl-1H-indole-3-carboxylate수율 96.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

NaH (60% dispersion in mineral oil, 8.56 g, 214.0 mmole) was added portionwise, allowing for gas evolution, to a solution of methyl 1H-indole-3-carboxylate (25.00 g, 142.7 mmole) in DMF (350 mL) at 0° C. When the NaH addition was complete, methyl iodide (44.4 mL, 713.5 mmole) was added at 0° C. The reaction was stirred at 0° C. for 15 minutes then at RT overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over K2CO3 and concentrated to afford the title compound (26.00 g, 96%) as an orange solid: MS (ES) m/e 190 (M+H)+.

후처리

  1. customat RT
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over K2CO3
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e33291da5609424f8925caf051acbfd2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741339B2

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