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

HRID 11064

反応式

HRID 11064 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8450601e0b244db8a4f671e080a931b1
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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