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

HRID 1866015Notes

Reaction equation

HRID 1866015 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.Br[CH2:28][C:29]1([F:33])[CH2:32][O:31][CH2:30]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][CH:25]=[CH:26][C:21]=5[CH2:20][O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:28][C:29]2([F:33])[CH2:32][O:31][CH2:30]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 221608003-(Bromomethyl)-3-fluorooxetane

Product 1

HCID 596576921'-({6-Chloro-1-[(3-fluorooxetan-3-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]

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 3-bromomethyl-3-fluoro-oxetane (described in US2005215599) gave the title compound. ES-MS m/e (%): 455.2 (M+H+).

Sources & evidence

ORD record
ord-7636f2da8fdc4e6a930156bbc9951674
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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