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

HRID 11063

Reaction equation

HRID 11063 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-612d771bad9043279bcecec1cba7a604
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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