تفاعل #425639

معادلة التفاعل

NaOH

SEM-chloride

5-bromo-6-methyl-indazole

dicyclohexylmethylamine

→

title compound

المردود 79.0%

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

المردود 79.0%

المذيبات

EtOAc

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر