Tetrabutylammonium Fluoride → tert-Butyl [3-nitro-1H-indol-4-yl]acetate

HRID 641404Notes

Reaction equation

HRID 641404 reaction equation
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:6](S(C2C=CC=CC=2)(=O)=O)[CH:5]=1)([O-:3])=[O:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57426199tert-Butyl [3-nitro-1-(phenylsulfonyl)-1H-indol-4-yl]acetate

Product 1

HCID 57426200tert-Butyl [3-nitro-1H-indol-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [3-nitro-1-(phenylsulfonyl)-1H-indol-4-yl]acetate from Step C (730 mg, 1.75 mmol) in THF (5 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 5.25 mL, 5.25 mmol) and the reaction mixture was stirred at ambient temperature for 10 min, then concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (5 mL) and extracted with CHCl3 (15 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CHCl3:EtOAc—90:10 to 50:50, to give the title compound. MS: m/z=221 (M−C4H7).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (5 mL)
  3. extractionextracted with CHCl3 (15 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of CHCl3

Sources & evidence

ORD record
ord-4b3f15ed0c3140d68eb19d808160f8e2
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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