4-(N-Ethylaminocarbonyl)phenylboronic acid → 4-[5-(4-Ethylcarbamoyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1471778

Reaction equation

HRID 1471778 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH:26][C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28])[CH3:25]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:32]4[CH:33]=[CH:34][C:29]([C:27](=[O:28])[NH:26][CH2:24][CH3:25])=[CH:30][CH:31]=4)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 34113074-(N-Ethylaminocarbonyl)phenylboronic acidHCID 866748894-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 717364164-[5-(4-Ethylcarbamoyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Procedure

The title compound is prepared from 4-(5-chloro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester and 4-ethylcarbamoyl-phenylboronic acid following a procedure analogous to that described for Example 1; the reaction is conducted at 150° C. LC (method 4): tR=1.68 min; Mass spectrum (ESI+): m/z=450 [M+H]+.

Workup

  1. customis conducted at 150° C

Sources & evidence

ORD record
ord-84755c5c51e145e583c4e8701482eec7
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Linked notes

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