Methyl iodide → Methyl 3-[N-methyl-3-(t-butylthio)-6-methoxyindol-2-yl]-2,2-dimethylpropanoate

HRID 327236노트

반응식

HRID 327236 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([S:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:8]([CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[NH:9]2)=[CH:5][CH:4]=1.[CH3:25][Si]([N-][Si](C)(C)C)(C)C.[K+].IC>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.C1(C)C=CC=CC=1>[CH3:25][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[C:7]([S:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:8]1[CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15]

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 53636575Methyl 3-[6-methoxy-3-(t-butylthio) indol-2-yl]-2,2-dimethylpropanoate

생성물 1

HCID 18947604Methyl 3-[N-methyl-3-(t-butylthio)-6-methoxyindol-2-yl]-2,2-dimethylpropanoate

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 12679Hexamethylphosphoramide용매

실험 절차

A solution of 1.75 g of the indole from Step A in 30 mL of THF and 3 mL HMPA was cooled to -78° C. and to this solution was slowly added a solution of 0.54M KHMDS in toluene (10.2 mL). The mixture was stirred at this temperature for 15 min. and treated with 0.34 mL of iodomethane. The mixture was stirred at -78° C. for 5 h, quenched with 1N HCl (100 mL), extracted with ethyl acetate, and the organic layer washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was chromatographed on flash silica gel using ethyl acetate:hexane (20:80) as eluant to afford the title compound as a solid; m.p. 97°-98° C.

후처리

  1. stirringThe mixture was stirred at -78° C. for 5 h
  2. customquenched with 1N HCl (100 mL)
  3. extractionextracted with ethyl acetate
  4. washthe organic layer washed with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue was chromatographed on flash silica gel

출처 및 근거

ORD 기록
ord-d688306480fd4054b5398cd2397616b0
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272145

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