反応 #469094

反応方程式

2-(2,2,2-Trifluoroethyl)-4-chloro-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

3,5-dichlorobenzeneboronic acid

CsF

→

title compound

収率 58.0%

2-(2,2,2-Trifluoroethyl)-4-(3,5-dichlorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

収率 58.0%

溶媒

DME

water

反応条件

後処理

1. 1
   温度heated
2. 2
   抽出extracted with ethyl acetate (100 mL)
3. 3
   洗浄The organic layer was washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   その他evaporated in vacuo
6. 6
   その他The compound was purified on a silica gel column
7. 7
   洗浄eluting with 30% ethyl acetate in pentanes

実験手順

2-(2,2,2-Trifluoroethyl)-4-chloro-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (150 mg, 0.409 mmol) (Example 193E) was dissolved in anhydrous DME (8 mL) and heated to reflux with 3,5-dichlorobenzeneboronic acid in presence of CsF (150 mg, 0.98 mmol) and tetrakis(triphenylphosphine)-palladium (17.38 mg, 0.015 mmol) for 6 hours. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate (100 mL). The organic layer was washed with brine, dried over MgSO4, and evaporated in vacuo. The compound was purified on a silica gel column, eluting with 30% ethyl acetate in pentanes, to provide the title compound (yield: 110 mg, 58%). 1H NMR (300 MHz, CDCl3) δ 3.08 (s, 3H), 4.88 (q, J=9 Hz, 2H), 7.06 (d, J=1.5 Hz, 9 Hz, 2H), 7.31 (t, J=1.5 Hz, 1H), 7.36 (d, J=9 Hz, 2H), 7.94 (s, 1H), 7.96 (d, J=9 Hz, 2H). MS (DCI/NH 3) m/z 496 (M+NH4)+. Anal. calc. for C19H13CI2F3N2O3S: C, 47.81; H, 2.75; N, 5.87. Found: C, 47.77; H, 2.75; N, 5.65

出典