Methyl iodide → 8-Fluoro-6-(4-fluoro-phenyl)-2-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925681ノート

反応式

HRID 925681 の反応式
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:8]2[N:7]3[CH2:18][CH2:19][NH:20][C:21](=[O:22])[C:6]3=[CH:5][C:4]=2[CH:3]=1.[H-].[Na+].I[CH3:26]>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:8]2[N:7]3[CH2:18][CH2:19][N:20]([CH3:26])[C:21](=[O:22])[C:6]3=[CH:5][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 900360598-Fluoro-6-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

生成物 1

HCID 900358568-Fluoro-6-(4-fluoro-phenyl)-2-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 8-fluoro-6-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 18) (0.05 g, 0.17 mmol) in DMF (1.1 ml) was added at room temperature sodium hydride (8.78 mg, 0.2 mmol), and the mixture was allowed to stir at room temperature for 30 min. Afterwards iodomethane (23.8 mg, 10.5 μl, 0.17 mmol) was added and the reaction mixture was allowed to stir at room temperature for 16 h. The mixture was poured into ice/water (30 ml) and extracted with ethyl acetate (2×25 ml). The combined organic layers were washed with brine (25 ml), dried (MgSO4) and evaporated. The crude product (50 mg) was further purified by flash chromatography on silica gel [dichloromethane-dichloromethane/MeOH 9:1 (0-50%)] to yield the title compound as a white solid (21 mg, 40%), MS (ISP) m/z=313.4 [(M+H)+], mp 212° C.

後処理

  1. stirringto stir at room temperature for 16 h
  2. extractionextracted with ethyl acetate (2×25 ml)
  3. washThe combined organic layers were washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product (50 mg) was further purified by flash chromatography on silica gel [dichloromethane-dichloromethane/MeOH 9:1 (0-50%)]

出典と根拠

ORDレコード
ord-35211e7b08744a9e9ac3e9c6c338cc13
出典データセット
uspto-grants-2016_03
特許番号
US09284321B2

反応ノート

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