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

HRID 6951노트

반응식

HRID 6951 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-657f79367abc4069a1261c2d77576d05
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084169B2

반응 노트

불러오는 중…