4-Chlorophenylboronic acid → 2-(4-Chloro-4''-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-4-methyl-pentanoic acid

HRID 426315Notes

Reaction equation

HRID 426315 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:13]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[Cl:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1>>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:14]2[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:34])=[O:3])[CH:11]=[C:12]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=3)[CH:13]=2)=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 577550554-Methyl-2-(5-trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 590047342-(4-Chloro-4''-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-4-methyl-pentanoic acid

Procedure

The title compound was prepared from a Suzuki coupling of 4-Methyl-2-(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (intermediate Example 1g) with 4-chlorophenylboronic acid under the conditions described in Example 1; 1H NMR (400 MHz, MeOD) δ ppm 0.87 (dd, J=6.60, 3.18 Hz, 6H), 1.41-1.51 (m, 1H), 1.65 (ddd, J=13.69, 7.21, 6.97 Hz, 1H), 1.95 (ddd, J=13.57, 7.70, 7.58 Hz, 1H), 3.74 (t, J=7.83 Hz, 1H), 7.33-7.40 (m, 2H), 7.50-7.59 (m, 4H), 7.65 (s, 1H), 7.67 (d, J=1.47 Hz, 2H), 7.75 (d, J=8.31 Hz, 2H); Calcd for C25H22ClF3O2 (M+H) 447.13, Found 447.

Sources & evidence

ORD record
ord-ed9369779a7643fcbdcd79427acb7553
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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