Tetrabutylammonium Fluoride → 2-tert-Butyl-1-methyl-5-nitro-1H-indole

HRID 503321Notes

Reaction equation

HRID 503321 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH:14][CH3:15].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:2]([C:3]1[N:14]([CH3:15])[C:6]2[C:5]([CH:4]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][CH:7]=2)([CH3:17])([CH3:16])[CH3:1]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59129150HCID 59129150, compound

Product 1

HCID 534211822-tert-Butyl-1-methyl-5-nitro-1H-indoleYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [2-(3,3-dimethyl-but-1-ynyl)-4-nitro-phenyl]-methyl-amine (5.0 g, 22.9 mmol) and TBAF (23.9 g, 91.6 mmol) in THF (50 mL) was heated at reflux overnight. The solvent was removed by evaporation under vacuum and the residue was dissolved in brine (100 mL) and EtOAc (100 mL). The organic phase was separated, dried over Na2SO4 and evaporated under vacuum to give 2-tert-butyl-1-methyl-5-nitro-1H-indole (5.0 g, 99%), which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.47 (d, J=2.4 Hz, 1H), 8.07 (dd, J=2.4, 9.2 Hz, 1H), 7.26-7.28 (m, 1H), 6.47 (s, 1H), 3.94 (s, 3H), 1.50 (s, 9H).

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed by evaporation under vacuum
  3. dissolutionthe residue was dissolved in brine (100 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-19961c377dcd436fb9d76452e935b3f4
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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