Methyl iodide → {2-[3-(2-fluoro-benzenesulfonyl)-1-methyl-1H-indol-7-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 6951ノート

反応式

HRID 6951 の反応式
[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[C:17]2[S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])(=[O:23])=[O:22])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:34]I>CN(C)C=O>[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[N:19]([CH3:34])[CH:18]=[C:17]2[S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])(=[O:23])=[O:22])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23544637{2-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 23544633{2-[3-(2-fluoro-benzenesulfonyl)-1-methyl-1H-indol-7-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A dry 25 mL flask equipped with a magnetic stirrer was charged with {2-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester (0.116 g., 0.258 mmol) and dimethylformamide (5 mL.) This solution was treated with sodium hydride (0.011 g. of 60% suspension in mineral oil, 0.284 mmol) and allowed to stir for 10 minutes under N2. Methyl iodide was then added via syringe in one portion. After 18 hours stirring at ambient temperature, the reaction mixture was extracted into 45 mL ethyl acetate and washed with water (2×45 mL). The organic fraction was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (85:15 hexanes:EtOAc to 70:30 hexanes:EtOAc) to give 45 mg of {2-[3-(2-fluoro-benzenesulfonyl)-1-methyl-1H-indol-7-yloxy]-ethyl}-methyl -carbamic acid tert-butyl ester as a clear oil: 1H NMR (CDCl3, 300 MHz) δ: 1.45 (s, 9H), 2.94 (s, 3H), 3.71 (m, 2H), 4.09 (s, 3H), 4.19 (m, 2H), 6.67 (d, 1H, J=7.7), 7.04 (m, 1H), 7.08 (t, 1H, J=8.0), 7.27 (td, 1H, J=7.6, J′=1.13), 7.44 (d, 1H, J=7.6), 7.49 (m, 1H), 7.74 (d, 1H, J=1.3), 8.15 (td, 1H, J=7.6, J′=1.8).

後処理

  1. customA dry 25 mL flask equipped with a magnetic stirrer
  2. stirringAfter 18 hours stirring at ambient temperature
  3. extractionthe reaction mixture was extracted into 45 mL ethyl acetate
  4. washwashed with water (2×45 mL)
  5. dry with materialThe organic fraction was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (85:15 hexanes:EtOAc to 70:30 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-657f79367abc4069a1261c2d77576d05
出典データセット
uspto-grants-2006_08
特許番号
US07084169B2

反応ノート

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