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

HRID 1623443Notes

Reaction equation

HRID 1623443 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[F:9].[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:6]3[CH:5]=[CH:4][C:3]([F:9])=[C:2]([Cl:1])[CH:7]=3)/[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)/[C:21]2=[O:30])[CH:14]=1

Participants

3

Reactant 2

HCID 27246052-Chloro-1-fluoro-4-iodobenzeneHCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 510335503-{3-[1-(3-Chloro-4-fluoro-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 2-chloro-1-fluoro-4-iodo-benzene (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), 7.50 (d, 1H), 7.22-7.42 (m, 9H), 7.09 (dt, 1H), 6.73 (dt, 1H), 6.66 (d, 1H), 6.51 (d, 1H), 4.95 (s, 2H), 3.91 (s, 3H).

Sources & evidence

ORD record
ord-043a6fc4b42f4aabb38bde954a3eac29
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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