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

HRID 426317Notes

Reaction equation

HRID 426317 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.[F:35][C:36]([F:47])([F:46])[C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1>>[F:31][C:30]([F:32])([F:33])[C:27]1[CH:28]=[CH:29][C:24]([C:12]2[CH:11]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:3])=[O:34])[CH:15]=[C:14]([C:40]3[CH:41]=[CH:42][C:37]([C:36]([F:47])([F:46])[F:35])=[CH:38][CH:39]=3)[CH:13]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 577550554-Methyl-2-(5-trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 510392362-(4,4''-Bis-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-trifluoromethyl-phenylboronic acid under the conditions described in Example 1; 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.93-1.02 (m, 6H), 1.59 (dt, J=13.39, 6.63 Hz, 1H), 1.79 (ddd, J=13.76, 7.34, 7.03 Hz, 1H), 2.08 (dt, J=13.69, 7.58 Hz, 1H), 3.84 (t, J=7.83 Hz, 1H), 7.26 (s, 2H), 7.58 (d, J=1.47 Hz, 2H), 7.68-7.75 (m, 7H).

Sources & evidence

ORD record
ord-fd6f998cc528498ebc345a6ba156b729
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

Loading…