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

HRID 18500

反応式

HRID 18500 の反応式
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

参加物

5

反応物 3

HCID 798Indole2 回HCID 10340Sodium CarbonateHCID 27822732-Propanone,3-bromo-1,1,1-trifluoro-, oxime

生成物 1

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

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b4ff9c053414483a8dc282ade2689add
出典データセット
uspto-grants-2010_06
特許番号
US07741361B2

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