3-{[(2-Iodo-phenyl)-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester → 3-{3-[2-(4-Chloro-phenyl)-1-phenyl-eth-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

HRID 1623474Notes

Reaction equation

HRID 1623474 reaction equation
[Br-].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Zn+])=[CH:5][CH:4]=1.[CH3:11][O:12][C:13](=[O:39])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2I)[C:22](=[O:31])[C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:15]=1>>[CH3:11][O:12][C:13](=[O:39])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)/[C:23](=[C:24](/[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)\[CH2:7][C:6]3[CH:9]=[CH:10][C:3]([Cl:2])=[CH:4][CH:5]=3)/[C:22]2=[O:31])[CH:15]=1

Participants

3

Reactant 2

HCID 670363063-{[(2-Iodo-phenyl)-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl esterHCID 178478119HCID 178478119, compound

Product 1

HCID 510345513-{3-[2-(4-Chloro-phenyl)-1-phenyl-eth-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 77 starting from 4-chloro-benzylzinc bromide (commercially available) and 3-{[(2-iodo-phenyl)-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester. 1H NMR (300 Hz, CDCl3): δppm 3.92 (s, 3H), 4.73 (s, 2H), 5.07 (s, 2H), 5.99 (d, 1H), 6.58-6.65 (m, 2H), 7.08-7.20 (m, 7H), 7.37-7.43 (m, 4H), 7.52 (d, 1H), 7.93 (d, 1H), 8.06 (s, 1H).

Sources & evidence

ORD record
ord-0a4e111fd05e41538becd0a722dc25b7
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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