反応 #44452

反応方程式

Water

methylzinc chloride

trans-N-(6-bromo-8-fluoro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Methylzinc chloride

→

trans-2,2,2-Trifluoro-N-(8-fluoro-2,3,4,14b-tetrahydro-6-methyl-1H-dibenzo[b,f]pyrido-[1,2-d][1,4]oxazepin-1-yl)acetamide

溶媒

THF

反応条件

後処理

1. 1
   温度the reaction mixture was heated at 80° C. for another hour
2. 2
   抽出the reaction mixture was extracted with ether and water
3. 3
   洗浄The ether solution was washed with brine
4. 4
   乾燥dried (Na2SO4)
5. 5
   その他the volatiles were removed under reduced pressure
6. 6
   その他After purification by HPLC the title compound
7. 7
   その他was obtained (108 mg, 39%)

実験手順

To a solution of trans-N-(6-bromo-8-fluoro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (300 mg, 0.65 mmol) in THF (7 mL) was added ferrocene PdCl2 (10 mg, 14 mmol) and the reaction mixture was stirred for 10 min. Methylzinc chloride (0.81 mL) was added dropwise whereafter the reaction mixture was heated to 60° C. After 3 h ferrocene PdCl2 (20 mg, 28 μmol) and methylzinc chloride (0.3 mL) were added and the reaction mixture was heated at 80° C. for another hour. Water was added at room temperature, and the reaction mixture was extracted with ether and water. The ether solution was washed with brine, dried (Na2SO4) and the volatiles were removed under reduced pressure. After purification by HPLC the title compound was obtained (108 mg, 39%). Data: 1H-NMR (400 MHz, CDCl3) 1.56-1.72 (m, 2H), 1.79-1.93 (m, 2H), 2.37 (s, 3H), 2.79-2.86 (m, 1H), 3.44-3.52 (td, J=12.0, J=3.0, 1H), 4.27-4.29 (d, J=2.5, 1H), 4.85-4.91 (m, 1H), 6.70-7.32 (6 ArH), 7.63-7.70 (br, 1H). (m/z)=395 (M+H)+.

出典