Potassium Carbonate → (3-Acetyl-5-trifluoromethoxy-indol-1-yl)-acetic acid tert-butyl ester

HRID 1527226ノート

反応式

HRID 1527226 の反応式
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13](=[O:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CC#N>[C:29]([O:28][C:26](=[O:27])[CH2:25][N:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:12][CH:11]=2)[C:7]([C:13](=[O:15])[CH3:14])=[CH:8]1)([CH3:32])([CH3:31])[CH3:30]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 682841811-(5-Trifluoromethoxy-1H-indol-3-yl)-ethanone

生成物 1

HCID 68284069(3-Acetyl-5-trifluoromethoxy-indol-1-yl)-acetic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

To a solution of 1-(5-trifluoromethoxy-1H-indol-3-yl)-ethanone (0.50 g, 2.06 mmol) in CH3CN (10 mL) was added K2CO3 (0.313 g, 2.26 mmol) and tert-butyl 2-bromoacetate (0.334 mL, 2.26 mmol). The reaction mixture was stirred at 90° C. overnight. The reaction mixture was filtered, and the filtrate was diluted with CH2Cl2. The organics were washed with 1M aqueous HCl solution (5 mL) and saturated aqueous NaHCO3 solution (5 mL). The organic layer was dried (phase separator) and evaporated in vacuo to afford the title compound as a yellowish oil: MS: 358.0 [M+H]+; tR (HPLC conditions c): 5.66 min. The material thus obtained was used directly in the next step without further purification.

後処理

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with CH2Cl2
  3. washThe organics were washed with 1M aqueous HCl solution (5 mL) and saturated aqueous NaHCO3 solution (5 mL)
  4. customThe organic layer was dried (phase separator)
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a92e47bc456043d59fbcd88e88346fb5
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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