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

HRID 384900Notes

Reaction equation

HRID 384900 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=1[O:18][CH3:19])=[O:10])([CH3:4])([CH3:3])[CH3:2].[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[N:34][CH:35]=1>>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:32]2[CH:33]=[N:34][CH:35]=[C:30]([F:29])[CH:31]=2)=[CH:13][C:12]=1[O:18][CH3:19])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 68408611Rac-[2-(4-bromo-2-methoxy-phenyl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68410960Rac-[1-(3,4-dichloro-phenyl)-2-[4-(5-fluoro-pyridin-3-yl)-2-methoxy-phenyl]-2-oxo-ethyl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared rac-[2-(4-bromo-2-methoxy-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): 507.4 (M+H)+ (100%) and 522.7 (M+NH4)+.

Sources & evidence

ORD record
ord-bc62dc2fdb2d4c38b515d83293aea620
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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