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

HRID 1527226노트

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HRID 1527226 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a92e47bc456043d59fbcd88e88346fb5
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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