Реакция #489283

Уравнение реакции

sodium carbonate

2-Naphthaleneboronic acid

4-bromoisoquinoline

triphenylphosphine

→

desired product

2-methyl-4-(naphthalen-2-yl)-1,2,3,4-tetrahydroisoquinoline

Растворители

1,2-dimethoxyethane

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was degassed with argon
2. 2
   Другоеthe suspension was degassed with argon
3. 3
   workup.STIRRINGAfter stirring at 85° C. for 3 hours
4. 4
   workup.ADDITIONthe cooled mixture was diluted with water
5. 5
   Экстракцияextracted with dichloromethane once
6. 6
   СушкаThe combined extracts were dried with sodium sulfate
7. 7
   Концентрированиеconcentrated under vacuum
8. 8
   Другоеpurified by chromatography (5:1 heptane/ethyl acetate)

Методика

2-Naphthaleneboronic acid (1.2 g, 7.2 mmol) was added to a solution of 4-bromoisoquinoline (1.0 g, 4.8 mmol) and triphenylphosphine (0.3 g, 0.9 mmol) in 1,2-dimethoxyethane (10 ml). The mixture was degassed with argon. Palladium(II) acetate (0.1 g, 0.5 mmol) was added and the suspension was stirred at room temperature for 20 minutes. Aqueous sodium carbonate (5.8 ml, 2 M) was added and the suspension was degassed with argon. After stirring at 85° C. for 3 hours, the cooled mixture was diluted with water and extracted with dichloromethane once. The combined extracts were dried with sodium sulfate, concentrated under vacuum and purified by chromatography (5:1 heptane/ethyl acetate) to give the desired product (1.1 g, 90%, 95% AUC GC): 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 8.62 (s, 1H), 7.92-8.12 (m, 6H), 7.56-7.72 (m, 5H).

Источник