Indole → 1,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime

HRID 1868404

반응식

HRID 1868404 반응식
Br[CH2:2][C:3](=[N:8][OH:9])[C:4]([F:7])([F:6])[F:5].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OC)(C)(C)C>[F:5][C:4]([F:7])([F:6])[C:3](=[N:8][OH:9])[CH2:2][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 798Indole2회HCID 10340Sodium CarbonateHCID 27822732-Propanone,3-bromo-1,1,1-trifluoro-, oxime

생성물 1

HCID 765493791,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime수율 89.2%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

To a solution of the 1.64 g (7.96 mmol) of 3-bromo-1,1,1-trifluoropropan-2-one oxime in 250 mL of methyl tert-butyl ether was added 3.74 g (31.92 mmol) of indole followed by 5.0 g (47.62 mmol) of powdered (freshly ground) sodium carbonate. The reaction was monitored by thin layer chromatography (ethyl acetate-hexanes (2:8)) to afford a new more polar product compared to indole (PMA-stained and UV-active). The mixture was then filtered through diatomaceous earth and concentrated in vacuo. The residue was then concentrated in vacuo and diluted first with dichloromethane (1 part) and then hexanes (4 parts) and passed through a pad of silica gel using dichloromethane-hexanes (gradient: 20%-100%) to afford 1.72 g (89.2%) of 1,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime as a white solid.

후처리

  1. customto afford a new more polar product
  2. filtrationThe mixture was then filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. concentrationThe residue was then concentrated in vacuo
  5. additiondiluted first with dichloromethane (1 part)

출처 및 근거

ORD 기록
ord-17a77fdf9e674e5b9d3fad3739dbfcc3
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635711B2

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