Indole → HCID 23294670, compound

HRID 1955110Notes

Reaction equation

HRID 1955110 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F>C1COCC1.C(OCC)(=O)C>[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1[N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 23294670HCID 23294670, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 334 mg(374 mg of 60% in oil, 9.35 mmol) of sodium hydride in 5 mL THF was treated with a solution of 1.0 g(8.5 mmol) of indole in 5 mL THF, followed by stirring at ambient temperature for 15 min. The solution was then treated with 1.35 g(8.5 mmol) of 3,4-difluoronitrobenzene. The solution was stirred at ambient temperature for 48 h, followed by concentration in vacuo to afford brown oil which was dissolved in ethyl acetate and washed with water. Drying (Na2SO4) and concentration in vacuo afforded an oil which was chromatographed over 100 g of 230-400 mesh silica gel, eluting with 20%(v/v) ethyl acetate in hexane. These procedures afforded 1.1 g(51%) of the title compound as a yellow solid. 1H NMR (CDCl3): δ8.23, 7.74, 7.40, 7.35, 7.30, 6.80.

Workup

  1. stirringThe solution was stirred at ambient temperature for 48 h
  2. concentrationfollowed by concentration in vacuo
  3. customto afford brown oil which
  4. washwashed with water
  5. customDrying
  6. concentration(Na2SO4) and concentration in vacuo
  7. customafforded an oil which
  8. customwas chromatographed over 100 g of 230-400 mesh silica gel
  9. washeluting with 20%(v/v) ethyl acetate in hexane

Sources & evidence

ORD record
ord-edb0404a59f8499597e72af5692f951d
Source dataset
uspto-grants-2000_09
Patent number
US06124334

Reaction notes

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