(3-Ethoxycarbonylphenyl)boronic acid → 3'-Chloro-4'-{2-[2-(3-ethoxycarbonyl-phenyl)-pyridin-4-yl]-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl}-biphenyl-3-carboxylic acid ethyl ester

HRID 1095897Notes

Reaction equation

HRID 1095897 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].[CH2:31]([O:33][C:34]([C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)=[O:35])[CH3:32]>>[CH2:31]([O:33][C:34]([C:36]1[CH:37]=[C:38]([C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([C:38]4[CH:39]=[CH:40][CH:41]=[C:36]([C:34]([O:33][CH2:31][CH3:32])=[O:35])[CH:37]=4)[CH:16]=3)([OH:14])[C:10]([F:11])([F:13])[F:12])=[C:2]([Cl:1])[CH:3]=2)[CH:39]=[CH:40][CH:41]=1)=[O:35])[CH3:32]

Participants

3

Reactant 2

HCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 86629107Trifluoro-methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl ester

Product 1

HCID 469401073'-Chloro-4'-{2-[2-(3-ethoxycarbonyl-phenyl)-pyridin-4-yl]-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl}-biphenyl-3-carboxylic acid ethyl ester

Procedure

In analogy to Example 49, trifluoromethanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl ester) (Example 26, step 1) was reacted with 3-ethoxycarbonylphenylboronic acid 4 h at 70° C. to give the title compound as a white solid. MS (m/e)=612.2 [M+H+].

Sources & evidence

ORD record
ord-b6137034c7854bc0af05e1b0c4028138
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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