Реакция #87701

Уравнение реакции

5-(2-chloro-6-fluorophenyl)-2-(4-ethynylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

4-chloro-2-fluoro-1-iodobenzene

TBAF

→

desired product

Выход 31.9%

5-(2-Chloro-6-fluorophenyl)-2-{4-[(4-chloro-2-fluorophenyl)ethynyl]pheny}-2,4-dihydro-3H-1,2,4-triazol-3-one

Выход 31.9%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   ДругоеThe title compound was prepared
2. 2
   ДругоеThe obtained crude product
3. 3
   Другоеwas purified with column chromatography on silica gel eluting with 1.0% MeOH

Методика

The title compound was prepared according to the procedure described in Example-3 using 5-(2-chloro-6-fluorophenyl)-2-(4-ethynylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (Intermediate-2, 0.100 g, 0.319 mmol), 4-chloro-2-fluoro-1-iodobenzene (0.123 g, 0.479 mmol), TBAF (0.201 g, 0.638 mmol), bis(triphenylphosphine)palladium(II) chloride (0.020 g, 0.028 mmol) and DMSO (3.0 ml). The obtained crude product was purified with column chromatography on silica gel eluting with 1.0% MeOH:DCM to afford 0.045 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.38 (d, J=8.4 Hz, 1H), 7.50 (t, J=8.7 Hz, 1H), 7.57-7.70 (m, 6H), 8.02 (d, J=8.7 Hz, 2H), 12.74 (br s, 1H). MS (m/z): 442.38 (M+).

Источник