3-(Methylsulfonyl)phenylboronic acid → Rac-[1-(3,4-dichloro-phenyl)-2-[5-(3-methanesulfonyl-phenyl)-pyridin-2-yl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 384909Notes

Reaction equation

HRID 384909 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][N:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:27][S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29]>>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH:36]=2)=[CH:13][N:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 68409891Rac-[2-(5-bromo-pyridin-2-yl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68408989Rac-[1-(3,4-dichloro-phenyl)-2-[5-(3-methanesulfonyl-phenyl)-pyridin-2-yl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared from rac-[2-(5-bromo-pyridin-2-yl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester and 3-methylsulfonylphenylboronic acid in analogy to Example 1b): MS (ISP): 535.1 and 536.1 (M+H)+, 479.1 and 481.0 ((M-isobutene)+H)+ (100%).

Sources & evidence

ORD record
ord-b394a735940346538d506c7e245b7f14
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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