1-Chloro-2-iodo-4-(trifluoromethyl)benzene → 3-{3-[1-(2-Chloro-5-trifluoromethyl-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

HRID 1623454Notes

Reaction equation

HRID 1623454 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1I.[CH3:13][O:14][C:15](=[O:40])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:24](=[O:33])[C:25]#[C:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:17]=1>>[CH3:13][O:14][C:15](=[O:40])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]2[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)/[C:25](=[C:26](\[C:3]3[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=3[Cl:1])/[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)/[C:24]2=[O:33])[CH:17]=1

Participants

3

Reactant 2

HCID 695961-Chloro-2-iodo-4-(trifluoromethyl)benzeneHCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 510350983-{3-[1-(2-Chloro-5-trifluoromethyl-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 1-chloro-2-iodo-4-trifluoromethyl-benzene (commercially available) and 3-{[phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester. 1H NMR (CDCl3, 300 MHz) δppm 8.01 (s, 1H), 7.93 (d, 1H), 7.63-7.67 (m, 2H), 7.33-7.52 (m, 7H), 7.10 (t, 1H), 6.64-6.71 (m, 2H), 5.98 (d, 1H), 4.87-5.04 (m, 2H), 3.91 (s, 3H).

Sources & evidence

ORD record
ord-6a879fa8fb5a4730a5309e7b7a96ae6e
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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