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| Typical applications of Bredereck's reagent（CAS:5815-08-7）（12） |
| 2022-06-20 |
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4-bromo-5-methyl-1H-indole(CAS: 610794-15-5)
To 2,6-dimethyl-3-nitrobromobenzene (2.31 g, 10.0 mmol) in anhydrous DMF (15 mL) is added Bredereck's reagent (tert-butoxybis(dimethylamino)methane) (4.35 mL, 21.1 mmol)
and the resultant solution is heated at 125 0C for 5h. Upon cooling to ambient temperature, the reaction mixture is diluted with water and extracted with methylene chloride.
The organic layer is isolated, dried (Na2SO4), filtered and concentrated in vacuo to give a dark brown oil.
The crude mixture is dissolved in acetic acid/water (12 mL of 4:1) and cooled to 0 °C prior to portion-wise addition of zinc dust (6.56 g, 100.4 mmol) over 2 h.
On completion of the addition the reaction mixture is stirred at ambient temperature for 1 h prior to heating at 110 0C for 2 h.
The resultant reaction mixture is passed through a pad of Celite eluting with methylene chloride.
The filtrate was extracted with methylene chloride and the organic layer is isolated, dried (Na2SO4), filtered and concentrated in vacuo.
The crude product is purified by silica gel column chromatography eluting with ethyl acetate/heptane to give 4-bromo-5-niethylindole as a dark brown oil which solidified on standing.
Ref：WO2008/79918, 2008, A1
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