(5-Fluoropyridin-3-yl)boronic acid → Rac-[1-(3,4-dichloro-phenyl)-2-[4-(5-fluoro-pyridin-3-yl)-2-methyl-phenyl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 384896Notes

Reaction equation

HRID 384896 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=1[CH3:18])=[O:10])([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1>>[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:31]2[CH:32]=[N:33][CH:34]=[C:29]([F:28])[CH:30]=2)=[CH:13][C:12]=1[CH3:18])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 68408658Rac-[2-(4-bromo-2-methyl-phenyl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68410335Rac-[1-(3,4-dichloro-phenyl)-2-[4-(5-fluoro-pyridin-3-yl)-2-methyl-phenyl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared from rac-[2-(4-bromo-2-methyl-phenyl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester and 5-fluoropyridine-3-boronic acid in analogy to Example 1b): MS (ISP): 489.1 and 491.2 (M+H)+.

Sources & evidence

ORD record
ord-1268ae0b9d33493185c06116eb02a4df
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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