反応 #680367

反応方程式

337c

1,2-Dimethyl-1H-imidazol-4-amine Hydrochloride

3,5-dibromo-1-methylpyridin-2(1H)-one

XantPhos

Cs2CO3

→

337d

収率 33.0%

5-Bromo-3-(1,2-dimethyl-1H-imidazol-4-ylamino)-1-methylpyridin-2(1H)-one

収率 33.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. 2
   その他After three cycles of vacuum/nitrogen flush
3. 3
   温度It was then cooled to room temperature
4. 4
   ろ過filtered
5. 5
   濃縮The filtrate was concentrated under reduced pressure
6. 6
   その他the resulting residue was purified by silica-gel column chromatography
7. 7
   洗浄eluting with dichloromethane/methanol (30:1 to 20:1)

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 337c (400 mg, 3.60 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (960 mg, 3.60 mmol), XantPhos (240 mg, 0.40 mmol), tris(dibenzylideneacetone)dipalladium(0) (360 mg, 0.40 mmol), Cs2CO3 (4.69 g, 14.4 mmol), and 1,4-dioxane (20 mL). After three cycles of vacuum/nitrogen flush, the mixture was heated at 90° C. for 2.5 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (30:1 to 20:1) to afford 337d as a pale yellow solid (350 mg, 33%). MS-ESI: [M+H]+ 297.1.

出典