Reaktion #425639

Reaktionsgleichung

NaOH

SEM-chloride

5-bromo-6-methyl-indazole

dicyclohexylmethylamine

→

title compound

Ausbeute 79.0%

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

Ausbeute 79.0%

Lösungsmittel

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle