Water → 2-Tert-butyl-6-fluoro-5-nitro-1H-indole

HRID 468317Notes

Reaction equation

HRID 468317 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([F:14])=[CH:7][C:6]=1[NH:15]C(=O)CCC.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>CN(C=O)C>[C:2]([C:3]1[NH:15][C:6]2[C:5]([CH:4]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([F:14])[CH:7]=2)([CH3:22])([CH3:21])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59129414N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide

Product 1

HCID 534211862-Tert-butyl-6-fluoro-5-nitro-1H-indoleYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide (3.0 g, 9.8 mmol) and TBAF (4.5 g, 17.2 mmol) in DMF (25 mL) was heated at 100° C. overnight. The mixture was poured into water and then extracted with EtOAc (80 mL×3). The combined extracts were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give compound 2-tert-butyl-6-fluoro-5-nitro-1H-indole (1.5 g, 65%). 1H-NMR (400 MHz, CDCl3) δ 8.30 (d, J=7.2 Hz, 1H), 7.12 (d, J=11.6 Hz, 1H), 6.35 (d, J=1.2 Hz, 1H), 1.40 (s, 9H).

Workup

  1. extractionextracted with EtOAc (80 mL×3)
  2. washThe combined extracts were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-ea79105d10e3435e89cccbb2e354fdfd
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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