(6-chloro-1H-indol-3-yl)-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylmethanone → 1'-{[6-Chloro-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-indol-3-yl]carbonyl}-3H-spiro[2-benzofuran-1,4'-piperidine]

HRID 2055539Notes

Reaction equation

HRID 2055539 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][CH:25]=[CH:26][C:21]=5[CH2:20][O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[O:27]1[CH2:32][CH2:31][CH:30]([CH2:33]COS(C)(=O)=O)[CH2:29][CH2:28]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][CH:25]=[CH:26][C:21]=5[CH2:20][O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:33][CH:30]2[CH2:31][CH2:32][O:27][CH2:28][CH2:29]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15951937(6-chloro-1H-indol-3-yl)-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylmethanoneHCID 222730832-(Tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate

Product 1

HCID 596576381'-{[6-Chloro-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-indol-3-yl]carbonyl}-3H-spiro[2-benzofuran-1,4'-piperidine]Yield 55%

Procedure

Following the general procedure III as described above, the alkylation of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] (prepared according to example 69) with commercially available methanesulfonic acid 2-(tetrahydro-pyran-4-yl)-ethylester (described in US 2004220214) gave the title compound in 55% yield. ES-MS m/e (%): 465.2(M+H+).

Sources & evidence

ORD record
ord-b763e2bdd99440cc80c53e1b8b08612b
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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