1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2(1H)-one → 4-[5-(1-Methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1184763Notes

Reaction equation

HRID 1184763 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][C:26]1=[O:40]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:28]4[CH:29]=[CH:30][N:25]([CH3:24])[C:26](=[O:40])[CH:27]=4)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 457865301-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2(1H)-oneHCID 866748954-(5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 679902064-[5-(1-Methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Procedure

The title compound is prepared from 4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester and 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one following a procedure analogous to that described in Example 28. LC (method 10): tR=1.61 min; Mass spectrum (ESI+): m/z=412 [M+H]+.

Sources & evidence

ORD record
ord-152f390a3816496d88132a5733f50372
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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