Ethyl Acetate → Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate

HRID 131641

反応式

HRID 131641 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]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

生成物 1

HCID 57431514Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate収率 61.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A suspension of 0.207 g (1 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 0.173 g (1.2 mmol) of 3-fluorobenzyl chloride and 0.276 g (2 mmol) of potassium carbonate in 10 ml of dimethylformamide is stirred at 60° C. for 24 hours. The reaction mixture is subsequently cooled and is poured into a mixture of ice-cold water and of ethyl acetate. After settling, the organic phase is separated and then it is washed with two times 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The solution is dried over magnesium sulfate and is filtered, and then the filtrate is concentrated under reduced pressure. 0.195 g of an oil is obtained, which oil is used as is in the following stage.

後処理

  1. temperatureThe reaction mixture is subsequently cooled
  2. customthe organic phase is separated
  3. washit is washed with two times 50 ml of water
  4. dry with materialThe solution is dried over magnesium sulfate
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated under reduced pressure

出典と根拠

ORDレコード
ord-276fbec6c06f45fea6c86055a2670eef
出典データセット
uspto-grants-2008_06
特許番号
US07384969B2

関連ノート

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