Maleimide → 3-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanenitrile

HRID 11064

반응식

HRID 11064 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[N:11]([CH2:21][CH2:22][C:23]#[N:24])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2.[C:25]1(=[O:31])[NH:29][C:28](=[O:30])[CH:27]=[CH:26]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:27]2[C:28](=[O:30])[NH:29][C:25](=[O:31])[C:26]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:21][CH2:22][C:23]#[N:24])[C:10]=2[CH:9]=1

참가 물질

3

반응물 2

HCID 10935MaleimideHCID 219807953-{2-[(E)-2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}propanenitrile

생성물 1

HCID 867602003-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanenitrile수율 80.2%

실험 절차

Diene (236) (1.30 g, 3.86 mmol) prepared as described in example 96 was reacted with maleimide (0.49 g) following The procedure described in example 68 and then aromatized according to the procedure described in example 70 to give crude material that was chromatographed on silica eluting with ethyl acetate/hexane (1:1). Trituration from methanol gave nitrile (237) (1.33 g, 80%) as a yellow powder, mp 287–288° C. 1H NMR δ [(CD3)2SO] 11.16 (br s, 1H), 8.53 (d, J=2.6 Hz, 1H), 8.02 (s, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.59 (m, 1H), 7.49 (m, 3H), 7.33 (dd, J=9.0, 2.6 Hz, 1H), 4.86 (t, J=6.7 Hz, 2H), 3.91 (s, 3H), 3.04 (t, J=6.7 Hz, 2H). Found: C, 65.32; H, 4.15; N, 9.60. C24H16ClN3O3.3/4H2O requires: C, 65.01; H, 3.98; N, 9.47.

후처리

  1. customto give crude material that
  2. customwas chromatographed on silica eluting with ethyl acetate/hexane (1:1)

출처 및 근거

ORD 기록
ord-8450601e0b244db8a4f671e080a931b1
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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