Phosphorus trichloride → 2-(4-Chlorophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile
반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]#[N:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N+:9]2[O-])=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]#[N:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1참가 물질
4
반응 조건
- 온도
- 60 °C
실험 절차
To a stirred solution of the crude intermediate 2-(4-chlorophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile 1-oxide (23 g, 0.06 mmol) in chloroform (230 mL) was added phosphorus trichloride (23 mL) and the reaction mixture was then heated at 60° C. After 2 h, the reaction was cooled to RT and ice-water added (ca. 200 mL). The organics were extracted into DCM (3×200 mL), dried (Na2SO4) and concentrated in vacuo to give (v) (20.3 g, 92%), which was used unpurified in subsequent steps. ESI-MS m/z calculated for [M+H]+: 339.1. found: 339.0. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.92-7.81 (m, 2H), 7.69-7.57 (m, 3H), 2.42-2.29 (m, 1H), 1.14-1.03 (m, 2H), 0.82-0.72 (m, 2H).