反応 #66303

反応方程式

dipropylamine

AlMe3

Rochelle's salt

(1E,4E)-ethyl 2-amino-8-bromo-3H-benzo[b]azepine-4-carboxylate

→

(1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide

収率 34.1%

溶媒

toluene

反応条件

後処理

1. 1
   その他A 50 ml round bottom flask equipped with a stir bar and nitrogen inlet
2. 2
   workup.ADDITIONOnce the addition
3. 3
   温度to warm to room temperature (˜20-30 minutes)
4. 4
   その他resulting in a dark solution
5. 5
   温度This mixture was warmed to 100° C. for about 16 hours
6. 6
   温度to cool to room temperature
7. 7
   抽出extracted with EtOAc (2×)
8. 8
   乾燥extracts dried over sodium sulfate
9. 9
   濃縮concentrated under reduced pressure

実験手順

A 50 ml round bottom flask equipped with a stir bar and nitrogen inlet was charged with 15 mls of dry toluene and dipropylamine (0.44 ml, 3.24 mmol). This was chilled to 0° C. and AlMe3 (4.04 mls, 8.09 mmol, 2M in toluene) was then added. Once the addition was complete, the mixture was allowed to warm to room temperature (˜20-30 minutes). (1E,4E)-ethyl 2-amino-8-bromo-3H-benzo[b]azepine-4-carboxylate (0.5 g, 1.62 mmol) was then added portionwise resulting in a dark solution. This mixture was warmed to 100° C. for about 16 hours, and then allowed to cool to room temperature. This mixture was then poured into 50 mls of a 30% aq. solution of Rochelle's salt and vigorously stirred for 20 minutes, then extracted with EtOAc (2×), extracts dried over sodium sulfate and concentrated under reduced pressure. Flash 40 Biotage (40M cartridge, 5% MeOH/DCM) afforded 201 mgs (32%) of (1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide. m/z (APCI-pos) M+1=364.2, 366.2.

出典