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2-(Bromomethyl)furan → 4-(6-fluoro-1-furan-2-ylmethyl-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester

HRID 457791
Notes
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Reaction equation

HRID 457791 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1>>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[N:14]([CH2:23][C:24]3[O:25][CH:26]=[CH:27][CH:28]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 46037652-(Bromomethyl)furanHCID 113237384-(6-fluoro-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester

Product 1

HCID 113492254-(6-fluoro-1-furan-2-ylmethyl-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl esterYield 100.5%

Procedure

This compound was obtained following procedure described in example 13 (part B) at room temperature for 5 hours, starting with 5 g (17.2 mmol) of 4-(6-fluoro-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester were and 3.2 g (20 mmol) of 2-bromomethyl-furan. After standard work-up, 6.4 g (99% of yield) of 4-(6-fluoro-1-furan-2-ylmethyl-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester were obtained.

Workup

custom
This compound was obtained

Sources & evidence

ORD record
ord-b6b8cf0fc646427497229658acfff45a
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07189741B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes