Реакция #425639

Уравнение реакции

NaOH

SEM-chloride

5-bromo-6-methyl-indazole

dicyclohexylmethylamine

→

title compound

Выход 79.0%

5-Bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole

Выход 79.0%

Растворители

EtOAc

THF

Условия реакции

Обработка

1. 1
   ДругоеThe layers were separated
2. 2
   Экстракцияthe aqueous layer was extracted with EtOAc (3×20 mL)
3. 3
   ПромывкаThe combined organic layers were washed consecutively with water and brine
4. 4
   СушкаThe organic layer was dried over Na2SO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe crude material was purified by flash chromatography (0-33% EtOAc/heptane)

Методика

To a solution of 5-bromo-6-methyl-indazole (500 mg, 2.37 mmol) in THF (6 mL) was added dicyclohexylmethylamine (0.63 mL, 3.0 mmol), followed by SEM-chloride (0.50 mL, 2.8 mmol) via syringe. The reaction mixture was stirred at room temperature for 3 hours. EtOAc (20 mL) was added followed by 0.5N aqueous NaOH (15 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed consecutively with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (0-33% EtOAc/heptane) to provide the title compound (639 mg, 79% yield). MS (ES+) 343.1 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.03 (s, 1H), 7.93 (s, 1H), 7.60 (s, 1H), 5.70 (s, 2H), 3.62 (t, J=8.10 Hz, 2H), 2.52 (s, 3H), 0.95 (t, J=8.30 Hz, 2H), 0.00 (s, 9H).

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