1'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one → 1'-{[6-Chloro-1-(pyrimidin-5-ylmethyl)-1H-indol-3-yl]carbonyl}-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

HRID 1865981Notes

Reaction equation

HRID 1865981 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=5[C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[N:29]1[CH:34]=[C:33]([CH2:35]OS(C)(=O)=O)[CH:32]=[N:31][CH:30]=1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=5[C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:35][C:33]2[CH:34]=[N:29][CH:30]=[N:31][CH:32]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 596576231'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-oneHCID 86610239Methanesulfonic acid pyrimidin-5-ylmethyl ester

Product 1

HCID 596576531'-{[6-Chloro-1-(pyrimidin-5-ylmethyl)-1H-indol-3-yl]carbonyl}-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Procedure

Following the general procedure III as described above, the alkylation of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (prepared according to example 19) with methanesulfonic acid pyrimidin-5-ylmethyl ester gave the title compound. ES-MS m/e (%): 491.0 (M+H+).

Sources & evidence

ORD record
ord-1a89879439e743b2892e7a85a28aa6a7
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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