反応 #1615146

反応方程式

pyridazine

(R)-3-(4-bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamide

N′″-(1,1-dimethylethyl)-N,N′,N″-tris[tris(dimethyl-amino)phosphoranylidene]-phosphorimidic triamide

→

title compound

収率 3.0%

(R)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one

収率 3.0%

溶媒

THF

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to −78° C.
2. 2
   workup.WAITto reach room temperature over 16 h
3. 3
   その他partitioned
4. 4
   乾燥The organic layer was dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated

実験手順

To a solution of pyridazine (250 mg, 3.12 mmol) and (R)-3-(4-bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamide (1.81 g, 4.99 mmol) in THF (10 mL) was added zinc iodide (996 mg, 3.12 mmol). The suspension was stirred for 10 min. at ambient temperature. The reaction mixture was cooled to −78° C., then N′″-(1,1-dimethylethyl)-N,N′,N″-tris[tris(dimethyl-amino)phosphoranylidene]-phosphorimidic triamide solution (“Schwesinger P4 base”; 1 M in hexane 4.68 mL, 4.68 mmol) was added. The reaction mixture was allowed to reach room temperature over 16 h, then partitioned between sat, aq. ammonium chloride solution and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound 30 mg, 3%), while the most of the starting material was recovered (1.51 g, 83%). Light yellow gum, MS: 381.1 [M+H]+.

出典