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

HRID 1769354ノート

反応式

HRID 1769354 の反応式
C[CH:2]([C:9]1NC2[C:16]([C:17]=1[S:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[CH:12]=2)[C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[K+].I[CH3:36].CN(P([N:45]([CH3:47])[CH3:46])(N(C)C)=O)C>C1COCC1.C1(C)C=CC=CC=1>[CH3:46][N:45]1[C:47]2[C:16](=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[CH:12]=2)[C:17]([S:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:9]1[CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([O:6][CH3:36])=[O:5]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 54438884Methyl 3-[6-methoxy-3-(t-butylthio) indol-2-yl]-2,2-dimethylpropanoic acid

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 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran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 HC1 (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 HC1 (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-a1e55bf3467c44e49f35021a8b9ade97
出典データセット
uspto-grants-1995_01
特許番号
US05380850

反応ノート

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