反应 #607479

反应方程式

101a

N-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)cyclobutanecarboxamide

{3-[(acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid

NaOAc

→

101b

收率 56.0%

[4-(5-cyclobutaneamido-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate

收率 56.0%

溶剂

acetonitrile

反应条件

后处理

1. 1
   其他A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. 2
   其他After three cycles of vacuum/argon flush
3. 3
   过滤It was then filtered
4. 4
   其他the filtrate was evaporated in vacuo
5. 5
   其他The residue was purified by silica-gel column chromatography
6. 6
   洗涤eluting with 20:1 dichloromethane/methanol

实验过程

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 101a (230 mg, 0.80 mmol), {3-[(acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid (320 mg, 0.80 mmol), Pd(dppf)Cl2 (42 mg, 0.050 mmol), NaOAc (82 mg, 1.0 mmol), K3PO4.3H2O (266 mg, 1.0 mmol), water (5 drops) and acetonitrile (6 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 1 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford 101b (200 mg, 56%) as a brown solid. MS-ESI: [M+H]+ 558.3

来源