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

HRID 468326Notes

Reaction equation

HRID 468326 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-7400089f2cb749ba883d297bb42dee44
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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