5-Iodo-1,2,3-trimethoxybenzene → 3-[2-Oxo-3-[1-phenyl-1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-2,3-dihydro-indol-1-ylmethyl]-benzoic acid methyl ester

HRID 1623444Notes

Reaction equation

HRID 1623444 reaction equation
I[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:14][O:15][C:16](=[O:41])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:25](=[O:34])[C:26]#[C:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:18]=1>>[CH3:14][O:15][C:16](=[O:41])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)/[C:26](=[C:27](/[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)\[C:2]3[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=3)/[C:25]2=[O:34])[CH:18]=1

Participants

3

Reactant 2

HCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 510336563-[2-Oxo-3-[1-phenyl-1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-2,3-dihydro-indol-1-ylmethyl]-benzoic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 5 starting from 5-Iodo-1,2,3-trimethoxy-benzene (commercially available) and 3-{[phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester. 1H NMR (300 Hz, CDCl3): δppm 3.76 (s, 6H), 3.91 (s, 3H), 3.94 (s, 3H), 4.96 (s, 2H), 6.55 (s, 2H), 6.61-6.71 (m, 4H), 7.06 (t, 1H), 7.38-7.40 (m, 5H), 7.53 (d, 1H), 7.91 (d, 1H), 8.02 (s, 1H).

Sources & evidence

ORD record
ord-13465ad2d345481a8a06af3ed042a1d1
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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