Water → 5-Fluoro-1-(4-methoxybenzyl)indoline-2,3-dione

HRID 15268

反応式

HRID 15268 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.O>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[C:6](=[O:11])[C:5]2=[O:12]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 2365665-Fluoroisatin

生成物 1

HCID 76771005-Fluoro-1-(4-methoxybenzyl)indoline-2,3-dione収率 80%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

実験手順

5-Fluoro-1H-indole-2,3-dione (956 mg, 5.79 mmol, 1 eq) was added as a solution in dry DMF to a stirred slurry of sodium hydride (278 mg, 11.6 mmol, 2 eq) in dry DMF drop wise over 15 minutes under an inert atmosphere with adequate pressure release to accommodate H2 evolution. The resulting mixture was stirred for 1 hour and p-methoxybenzyl chloride was added via syringe to the reaction. The solution was then stirred ca 2 hours and worked up by addition of water followed by extraction into ethyl acetate. The organic layer was washed twice with water and then dried over MgSO4. Column chromatography with ethyl acetate/hexane afforded 5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione as a red solid (1.3 g, 80% yield). 1H NMR (CDCl3) δ (ppm): 7.3-7.24 (m, 3H), 7.20 (td, J=8.7, 2.7 Hz, 1H), 6.9-6.86 (m, 2H), 6.76 (dd, J=8.6, 3.6 Hz, 1H), 3.81 (s, 2H), 3.78 (s, 3H). LC/MS=286.1 (M+1).

後処理

  1. stirringThe solution was then stirred ca 2 hours
  2. extractionfollowed by extraction into ethyl acetate
  3. washThe organic layer was washed twice with water
  4. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-dbc008b6d4344431a0479a5e6a29980f
出典データセット
uspto-grants-2010_06
特許番号
US07732449B2

関連ノート

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