Reacción #607479

Ecuación de reacción

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

Rendimiento 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

Rendimiento 56.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. 2
   OtroAfter three cycles of vacuum/argon flush
3. 3
   FiltraciónIt was then filtered
4. 4
   Otrothe filtrate was evaporated in vacuo
5. 5
   OtroThe residue was purified by silica-gel column chromatography
6. 6
   Lavadoeluting with 20:1 dichloromethane/methanol

Procedimiento

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

Fuente