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

HRID 11063

반응식

HRID 11063 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-612d771bad9043279bcecec1cba7a604
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

연결된 노트

불러오는 중…