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

HRID 1623458Notes

Reaction equation

HRID 1623458 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].[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:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][CH3:9])/[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 28014161-Iodo-2-methylsulfanylbenzeneHCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 510349873-{3-[1-(2-Methylsulfanyl-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-iodo-2-methylsulfanyl-benzene (commercially available) and 3-{[phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester. 1H NMR (300 Hz, CDCl3): δppm 2.31 (s, 3H), 3.90 (s, 3H), 5.00 (dd, 2H), 6.03 (d, 1H), 6.60-6.64 (m, 2H), 7.04 (t, 1H), 7.26-7.30 (m, 2H), 7.33-7.56 (m, 9H), 7.95 (d, 1H), 8.01 (s, 1H).

Sources & evidence

ORD record
ord-b98edc205497467ea3f3d2bbc5d15495
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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