Tetrabutylammonium Fluoride → HCID 57908191, compound

HRID 513074Notes

Reaction equation

HRID 513074 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5]1[C:6]([NH2:14])=[N:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:2]([C:3]1[NH:14][C:6]2=[N:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:5]2[CH:4]=1)([CH3:16])([CH3:15])[CH3:1]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57908197HCID 57908197, compound

Product 1

HCID 57908191HCID 57908191, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(3,3-dimethylbut-1-ynyl)-5-nitropyridin-2-amine (0.4 g, 1.8 mmol) and TBAF (1.9 g, 7.3 mmol) in THF (10 mL) was heated at reflux overnight. The reaction mixture was concentrated to dryness under vacuum, and the residue was dissolved in ethyl acetate (20 mL). The organic layer was washed with water, brine, dried over Na2SO4 and concentrated under vacuum to afford 2-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.25 g, 63%). 1H-NMR (CDCl3, 400 MHz) δ 11.15 (brs, 1H), 9.20 (s, J=2.0 Hz, 1H), 8.70 (d, J=2.0 Hz, 1H), 6.43 (d, J=1.6 Hz, 1H), 1.51 (s, 9H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated to dryness under vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a6083f9bdb834125bc71ccda856e1f0d
Source dataset
uspto-grants-2015_08
Patent number
US09102672B2

Reaction notes

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