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6-Chloro-4-methylpyridine-3-boronic acid → 4-[5-(6-Chloro-4-methyl-pyridin-3-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester

HRID 1184702
Notes
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Reaction equation

HRID 1184702 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19](Br)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27](B(O)O)=[CH:26][N:25]=1>>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:27]4[CH:26]=[N:25][C:24]([Cl:23])=[CH:29][C:28]=4[CH3:30])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 441191696-Chloro-4-methylpyridine-3-boronic acidHCID 679732624-(5-Bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 866748914-[5-(6-Chloro-4-methyl-pyridin-3-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester

Procedure

The title compound is prepared from 4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid isopropyl ester and 2-chloro-4-methylpyridine-5-boronic acid following a procedure analogous to that described for Intermediate 15. LC (method 6): tR=1.40 min; Mass spectrum (ESI+): m/z=415 [M+H]+.

Sources & evidence

ORD record
ord-671eb2eebe844e679d5c0c9b59178949
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669271B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes