4-Iodobenzonitrile → 3-{3-[1-(4-Cyano-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

HRID 1623441Notes

Reaction equation

I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12](=[O:37])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:21](=[O:30])[C:22]#[C:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=1>>[CH3:10][O:11][C:12](=[O:37])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]2[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)/[C:22](=[C:23](\[C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)/[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)/[C:21]2=[O:30])[CH:14]=1

Participants

Reactant 2

HCID 764674-Iodobenzonitrile

HCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 510335483-{3-[1-(4-Cyano-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 5 starting from 4-iodo-benzonitrile (commercially available) and 3-{[phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester. 1H NMR (CDCl3, 300 MHz) δppm 8.00 (s, 1H), 7.93 (d, 1H), 7.74-7.76 (m, 2H), 7.35-7.51 (m, 9H), 7.10 (t, 1H), 6.56-6.72 (m, 2H), 6.35 (d, 1H), 4.95 (s, 2H), 3.91 (s, 3H)

Sources & evidence

ORD record: ord-422791272dfd47eb85b592dd1043ed4e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778973B2

Reaction notes

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