4-(2-Bromoethyl)oxane → 1'-({6-Chloro-1-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one hydrochloride

HRID 1865999Notes

Reaction equation

HRID 1865999 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.Br[CH2:30][CH2:31][CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[ClH: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[CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 226370124-(2-Bromoethyl)oxaneHCID 596576231'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Product 1

HCID 690141761'-({6-Chloro-1-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one hydrochloride

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 4-(2-bromo-ethyl)-tetrahydro-pyran (described in US 2004220214) gave the title compound. ES-MS m/e (%): 511.2 (M+H+).

Sources & evidence

ORD record
ord-0e0baf8e306a4427bbb14c1fdf91dd89
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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