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

HRID 1095895Notes

Reaction equation

HRID 1095895 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:21])[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:41]=[C:40]([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]([Cl:21])[CH:16]=3)([OH:14])[C:10]([F:12])([F:11])[F:13])=[C:2]([Cl:1])[CH:3]=2)[CH:39]=[CH:38][CH:37]=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 469400223'-Chloro-4'-[2-(2-chloro-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 at 70° C. 4 h to give the title compound as a colorless white solid. MS (m/e)=498.1 [M+H+].

Sources & evidence

ORD record
ord-5dcc5803f88a4e0286262f755df22c14
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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