反応 #163321

反応方程式

5-bromo-2-((tert-butyldimethylsilyl)ethynyl)pyridine

methanol

p-tolyl-boronic acid

Na2CO3

→

desired product

2-((tert-Butyldimethylsilyl)ethynyl)-5-p-tolylpyridine

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度at reflux for 2 h
2. 2
   その他Then the solvent is removed in vacuo to some extent
3. 3
   workup.ADDITIONthe residue is diluted with EtOAc and water
4. 4
   洗浄The organic layer is sequently washed with 50 mL half sat. Na2CO3 solution (1×) and 50 mL water (1×)
5. 5
   乾燥The organic layer is dried with MgSO4
6. 6
   その他the solvent is removed in vacuo
7. 7
   workup.ADDITIONThe residue is treated with DIPE and PE
8. 8
   ろ過is filtered
9. 9
   その他dried

実験手順

4.6 g (15.00 mmol) 5-bromo-2-((tert-butyldimethylsilyl)ethynyl)pyridine are added to 12 mL methanol and 50 mL 1,4-dioxane. Then the mixture is charged with 2.40 g (17.3 mmol) p-tolyl-boronic acid, 0.1 g (0.15 mmol) bis(triphenyphosphine)-dichloropalladium and 16.5 mL (33.0 mmol) of a 2N aq. Na2CO3 solution. The reaction mixture is stirred at reflux for 2 h. Then the solvent is removed in vacuo to some extent and the residue is diluted with EtOAc and water. The organic layer is sequently washed with 50 mL half sat. Na2CO3 solution (1×) and 50 mL water (1×). The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The residue is treated with DIPE and PE to receive a precipitate which is filtered and dried to yield the desired product.

出典