trans-2-[4-(Trifluoromethyl)phenyl]vinylboronic acid → 4-Methyl-2-{4'-trifluoromethyl-5-[2-(4-trifluoromethyl-phenyl)-vinyl]-biphenyl-3-yl}-pentanoic acid
Reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10](C2C=CC=CC=2)[CH:11]=[C:12](C(F)(F)F)[CH:13]=1)[C:5]([OH:7])=[O:6].[F:25][C:26]([F:39])([F:38])[C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/B(O)O)=[CH:29][CH:28]=1>>[CH3:24][CH:2]([CH3:1])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10]([C:30]2[CH:31]=[CH:32][C:27]([C:26]([F:39])([F:38])[F:25])=[CH:28][CH:29]=2)[CH:11]=[C:12]([CH:34]=[CH:33][C:30]2[CH:31]=[CH:32][C:27]([C:26]([F:39])([F:38])[F:25])=[CH:28][CH:29]=2)[CH:13]=1)[C:5]([OH:7])=[O:6]Participants
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-(4-trifluoromethylphenyl)-vinyl-boronic acid under the conditions described in Example 14; 1H NMR (400 MHz, MeOD) δ ppm 0.78-0.89 (m, 6 H), 1.47 (dt, J=13.39, 6.63 Hz, 1 H), 1.62 (ddd, J=13.63, 7.09, 6.91 Hz, 1 H), 1.91-1.98 (m, 1 H), 3.68 (t, J=7.83 Hz, 1 H), 7.33 (d, J=16.4 Hz, 1 H), 7.26 (d, J=16.5 Hz, 1 H), 7.48-7.58 (m, 4 H), 7.64-7.70 (m, 5 H), 7.75-7.78 (m, 2 H).
Sources & evidence
- ORD record
- ord-ad5bff7f18ab4119b5e40f3ed35c0c35
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08692017B2
Reaction notes
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