反应 #355777

反应方程式

2-chloro-4-methylpyridine

4-(methylsulfonyl)phenylboronic acid

potassium phosphate

→

title compound

收率 74.0%

2-[4-(methylsulfonyl)phenyl]-4-methylpyridine

收率 74.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度the reaction was cooled
2. 2
   其他the DMF removed in vacuo
3. 3
   其他The residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
4. 4
   其他separated
5. 5
   干燥the organic layer dried over sodium sulfate
6. 6
   浓缩concentrated in vacuo
7. 7
   其他Purification by silica chromatography
8. 8
   洗涤eluting with a gradient of ethyl acetate in cyclohexane

实验过程

To a mixture of 2-chloro-4-methylpyridine (3 g, 23.5 mmol), 4-(methylsulfonyl)phenylboronic acid (5.64 g, 28.2 mmol), potassium phosphate (12.0 g, 56.4 mmol) and DMF (50 mL) under an atmosphere of nitrogen was added palladium tetrakistriphenylphosphine (1.36 g, 1.18 mmol). After heating at 120° C. for 14 hours, the reaction was cooled and the DMF removed in vacuo. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL), separated and the organic layer dried over sodium sulfate and concentrated in vacuo. Purification by silica chromatography eluting with a gradient of ethyl acetate in cyclohexane gave the title compound (4.29 g, 74%) TLC RF 0.19 (1:1 ethyl acetate:cyclohexane) LC retention time 2.36 mins, MS m/z 248 (MH+)

来源