Реакция #2452600

Уравнение реакции

6-bromo-1-methyl-1H-indole-2-carbaldehyde

MeNO2

→

title compound

Выход 99.0%

6-Bromo-1-methyl-2-(2-nitrovinyl)-1H-indole

Выход 99.0%

Условия реакции

Обработка

1. 1
   Температураto reflux for 2 h
2. 2
   Другоеpartitioned between water and EtOAc
3. 3
   ДругоеThe aqueous phase was separated
4. 4
   Экстракцияextracted with EtOAc (3×)
5. 5
   СушкаThe organic extracts were dried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated

Методика

A solution of 6-bromo-1-methyl-1H-indole-2-carbaldehyde (422 mg, 1.77 mmol) and NH4OAc (137 mg, 1.77 mmol) in MeNO2 (10.0 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature and partitioned between water and EtOAc. The aqueous phase was separated and extracted with EtOAc (3×). The organic extracts were dried over Na2SO4, filtered and concentrated to give title compound (490 mg, 99%) as an orange solid: 1H NMR (500 MHz, CDCl3) δ 8.12 (d, J=13.0 Hz, 1H), 7.67 (d, J=13.5 Hz, 1H), 7.53 (s, 1H), 7.50 (d, J=8.5 Hz, 1H), 7.26 (dd, J=8.5, 1.5 Hz, 1H), 7.05 (s, 1H), 3.84 (s, 3H).

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