3-(Bromomethyl)-3-fluorooxetane → 1'-({6-Chloro-1-[(3-fluorooxetan-3-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

HRID 1865996Notes

Reaction equation

HRID 1865996 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[C:20](=[O:27])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Br[CH2:29][C:30]1([F:34])[CH2:33][O:32][CH2:31]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[C:20](=[O:27])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:29][C:30]2([F:34])[CH2:33][O:32][CH2:31]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 221608003-(Bromomethyl)-3-fluorooxetaneHCID 596575991'-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Product 1

HCID 596577101'-({6-Chloro-1-[(3-fluorooxetan-3-yl)methyl]-1H-indol-3-yl}carbonyl)-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]-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (prepared according to example 16 above) with 3-bromomethyl-3-fluoro-oxetane (described in US2005215599) gave the title compound. ES-MS m/e (%): 469.2 (M+H+).

Sources & evidence

ORD record
ord-d6b671e3e1934a4a8ee52ccbd79c8c86
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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