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

HRID 1868404Notes

Reaction equation

HRID 1868404 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-17a77fdf9e674e5b9d3fad3739dbfcc3
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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