2-tert-butyl-1-methyl-5-nitro-1H-indole synthesis

5synthesis methods

Product Name:2-tert-butyl-1-methyl-5-nitro-1H-indole
CAS Number:952664-81-2
Molecular formula:C13H16N2O2
Molecular Weight:232.28

Benzenamine, 2-(3,3-dimethyl-1-butyn-1-yl)-N-methyl-4-nitro-

952664-80-1
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952664-81-2
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Yield:952664-81-2 99%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran;Heating / reflux;

Steps:

32

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 Na₂SO₄and 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).

References:

US2007/244159,2007,A1 Location in patent:Page/Page column 116-117