Acrylonitrile → 3-{2-[(E)-2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}propanenitrile

HRID 11063

反応式

HRID 11063 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[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2.OC1C=CC2[NH:31][C:30]3C=C(C4C=C([N+]([O-])=O)C=CC=4O)C4C(=O)NC(=O)C=4[C:25]=3[C:24]=2C=1.C(#N)C=C>C(#N)C.N12CCCN=C1CCCCC2.O>[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]([CH2:24][CH2:25][C:30]#[N:31])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2

参加物

7

反応物 3

HCID 7855AcrylonitrileHCID 695838012-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indoleHCID 697127339-Hydroxy-4-(2-hydroxy-5-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

生成物 1

HCID 219807953-{2-[(E)-2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}propanenitrile収率 77%

試薬・触媒・溶媒 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of trans-diene (27) prepared as described in example 37 (1.5 g, 5.25 mmol) in acetonitrile (30 mL) was added acrylonitrile (2.42 mL, 36.8 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (20 drops). The resulting solution was stirred at room temperature under nitrogen for 18 h before being diluted with water and extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetate/hexane (1:1), followed by trituration from methanol gave the diene (236) (1.36 g, 77%) as an off-white solid, mp 136–138° C. 1H NMR δ [(CD3)2SO] 8.05 (dd, J=7.9, 1.5 Hz, 1H), 7.50 (m, 4H), 7.41 (m, 1H), 7.33 (m, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.90 (s, 1H), 6.81 (dd, J=9.0, 2.4 Hz, 1H), 4.68 (t, J=6.6 Hz, 2H), 3.77 (s, 3H), 2.93 (t, J=6.6 Hz, 2H). Found: C, 71.32; H, 5.14; N, 8.51. C20H17ClN2O requires: C, 71.31; H, 5.09; N, 8.31.

後処理

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. customthe drying agent was removed
  4. concentrationthe solution was concentrated to dryness

出典と根拠

ORDレコード
ord-612d771bad9043279bcecec1cba7a604
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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