Реакция #44452

Уравнение реакции

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

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated at 80° C. for another hour
2. 2
   Экстракцияthe reaction mixture was extracted with ether and water
3. 3
   ПромывкаThe ether solution was washed with brine
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Другоеthe volatiles were removed under reduced pressure
6. 6
   ДругоеAfter purification by HPLC the title compound
7. 7
   Другоеwas obtained (108 mg, 39%)

Методика

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)+.

Источник