Реакция #2358521

ord-c486dd16e6c14a00b2e48518359803fe

Уравнение реакции

ClCCl
CH2Cl2
CS(=O)(=O)c1cc(F)cc(OCCBr)c1
1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene
C1CNC1
azetidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CS(=O)(=O)c1cc(F)cc(OCCN2CCC2)c1
1-[2-(3-fluoro-5-methylsulfonyl-phenoxy)ethyl]azetidine

Растворители

Условия реакции

Температура
120°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураThe reaction mixture was cooled to room temperature
  2. 2
    Фильтрацияsolids was filtered off
  3. 3
    Другоеthe volatiles were evaporated
  4. 4
    Другоеre-crystallized from methanol/diethyl ether

Методика

1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.6 mmol), azetidine (0.23 ml, 3.2 mmol) and potassium carbonate (0.58 g, 4.2 mmol) was dissolved in acetonitrile (10 ml). The mixture was heated in a sealed container at 120° C. for 2 h. The reaction mixture was cooled to room temperature, CH2Cl2 (100 ml) was added, solids was filtered off and the volatiles were evaporated. The amine was converted to the fumaric acid salt and re-crystallized from methanol/diethyl ether. MS m/z (relative intensity, 70 eV) 273 (M+, 1), 94 (5), 82 (3), 71 (5), 70 (bp).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09120728B2uspto-grants-2015_09