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Methyl iodide → N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-N-methyl methanesulfonamide

HRID 502164
ノート
印刷プレビュー

反応式

HRID 502164 の反応式
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=1)#[N:2].[H-].[Na+].I[CH3:30]>CN(C=O)C.O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:30])[S:23]([CH3:26])(=[O:24])=[O:25])=[CH:18][CH:17]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59425187N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]methanesulfonamide

生成物 1

HCID 59425065N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-N-methyl methanesulfonamide収率 45%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]methanesulfonamide (130 mg, 0.35 mmol), prepared as in Example 1Y, in DMF (10 mL) is treated with NaH (21 mg, 0.53 mmol), and stirred at room temperature for 10 min. Iodomethane (0.03 mL, 0.53 mmol) is added, and the mixture is stirred at room temperature for 18 h. The reaction mixture is then diluted with H2O, and extracted with EtOAc (2×). The organic phases are washed with H2O and saturated NaCl and then dried and concentrated. Purification by flash chromatography over silica gel (EtOAc/CH2Cl2, 0-1%) gives 60 mg (45%) of N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-N-methyl methanesulfonamide as a white solid.

後処理

  1. stirringthe mixture is stirred at room temperature for 18 h
  2. extractionextracted with EtOAc (2×)
  3. washThe organic phases are washed with H2O and saturated NaCl
  4. customdried
  5. concentrationconcentrated
  6. customPurification by flash chromatography over silica gel (EtOAc/CH2Cl2, 0-1%)

出典と根拠

ORDレコード
ord-66bfbd8263d84479ae332decd3a152c0
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772271B2

反応ノート

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