반응 #85719

반응 방정식

1H-pyrazole-3-carbaldehyde

1-chloro-4-iodobenzene

(1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine

K2CO3

→

1-(4-chlorophenyl)-1H-pyrazole-3-carbaldehyde

수율 56.9%

용매

toluene

water

반응 조건

후처리

1. 1
   기타The reaction was sealed
2. 2
   온도The reaction mixture was then cooled to room temperature
3. 3
   추출extracted with EtOAc (3×30 mL)
4. 4
   건조The combined organic was then dried (Na2SO4)
5. 5
   농축concentrated

실험 절차

To a mixture of 1H-pyrazole-3-carbaldehyde (1.52 g, 15.82 mmol), 1-chloro-4-iodobenzene (5.66 g, 23.73 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (0.450 g, 3.16 mmol), copper(I) iodide (0.151 g, 0.791 mmol) and K2CO3 (4.37 g, 31.6 mmol) was added toluene (20 mL). The reaction was sealed and heated to 110° C. for 18 hours. The reaction mixture was then cooled to room temperature and diluted with water (50 mL), and extracted with EtOAc (3×30 mL). The combined organic was then dried (Na2SO4) and concentrated to give crude 1-(4-chlorophenyl)-1H-pyrazole-3-carbaldehyde (1.86 g, 9.0 mmol), to which was added (R)-2-methylpropane-2-sulfinamide (1.20 g, 9.90 mmol), CuSO4 (2.155 g, 13.50 mmol) and DCE (30 ml). The reaction was sealed, heated at 60° C. for 18 hours. A dark green suspension resulted. The reaction mixture was then cooled to 20° C., filtered through a pad of celite, rinsed with DCM. The solution was then concentrated to give final crude product as a light green oil. The residue was purified via silica gel chromatography (EtOAc/Heptane). LCMS (B) m/z 310.3 (M+H)+

출처