4-Methyl-2-(5-trifluoromethyl-biphenyl-3-yl)pentanoic acid → 2-{5-[2-(3,5-Bis-trifluoromethyl-phenyl)-vinyl]-4'-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid
Reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=[C:12](C(F)(F)F)[CH:13]=1)[C:5]([OH:7])=[O:6].[F:25][C:26]([F:43])([F:42])[C:27]1[CH:28]=[C:29](/[CH:37]=[CH:38]/B(O)O)[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1>>[F:25][C:26]([F:43])([F:42])[C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][C:12]2[CH:13]=[C:8]([CH:4]([CH2:3][CH:2]([CH3:1])[CH3:24])[C:5]([OH:7])=[O:6])[CH:9]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:26]([F:43])([F:42])[F:25])=[CH:20][CH:19]=3)[CH:11]=2)[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1Participants
3
Procedure
The title compound was prepared from a Nigishi coupling of 4-methyl-2-(5-trifluoromethyl-biphenyl-3-yl)pentanoic acid (intermediate compound 1g) with trans-2-(3,5-bis-trifluoromethylphenyl)-vinyl-boronic acid under the conditions described in Example 14; 1H NMR (400 MHz, MeOD) δ ppm 0.98 (dd, J=6.60, 3.18 Hz, 6 H), 1.56 (dt, J=13.39, 6.63 Hz, 1 H), 1.75 (ddd, J=13.69, 7.21, 6.97 Hz, 1 H), 2.05 (ddd, J=13.57, 7.70, 7.58 Hz, 1 H), 3.82 (t, J=7.70 Hz, 1 H), 7.52 (d, J=16.5 Hz, 1 H), 7.44 (d, J=16.5 Hz, 1 H), 7.60 (s, 1 H), 7.67 (s, 1 H), 7.74-7.84 (m, 6 H), 8.18 (s, 2 H); Calcd for C29H23F9O2 (M+H) 575.16, Found 575.1.
Sources & evidence
- ORD record
- ord-67263ceb2e5c4e1cb2340e6ae55270a4
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08692017B2
Reaction notes
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