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

HRID 327236ノート

反応式

HRID 327236 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 12679Hexamethylphosphoramide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d688306480fd4054b5398cd2397616b0
出典データセット
uspto-grants-1993_12
特許番号
US05272145

反応ノート

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