2-tert-butyl-6-fluoro-5-nitro-1H-indole synthesis
- Product Name:2-tert-butyl-6-fluoro-5-nitro-1H-indole
- CAS Number:952664-72-1
- Molecular formula:C12H13FN2O2
- Molecular Weight:236.24
![Butanamide, N-[2-(3,3-dimethyl-1-butyn-1-yl)-5-fluoro-4-nitrophenyl]-](/CAS/20210111/GIF/952664-71-0.gif)
952664-71-0
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Yield:952664-72-1 65%
Reaction Conditions:
with tetrabutyl ammonium fluoride in N,N-dimethyl-formamide at 100;
Steps:
30
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).
References:
US2007/244159,2007,A1 Location in patent:Page/Page column 113
2369-13-3
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