1-Ethynyl-4-(trifluoromethyl)benzene → 4-Methyl-2-[4'-trifluoromethyl-5-(4-trifluoromethyl-phenylethynyl)-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].[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)#[CH:26]>>[CH3:24][CH:2]([CH3:1])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH:11]=[C:12]([C:26]#[C:25][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)[CH:13]=1)[C:5]([OH:7])=[O:6]Participants
3
Procedure
The title compound was prepared from a Sonogashira coupling of 4-methyl-2-(5-trifluoromethyl-biphenyl-3-yl)pentanoic acid (intermediate compound 1g) with 1-ethynyl-4-trifluoromethyl-benzene under the conditions described in Example 10; 1H NMR (400 MHz, MeOD) δ ppm 0.86 (dd, J=6.60, 1.96 Hz, 6 H), 1.44 (dt, J=13.45, 6.72 Hz, 1 H), 1.62 (ddd, J=13.82, 7.09, 6.97 Hz, 1 H), 1.87-1.97 (m, 1 H), 3.70 (t, J=7.83 Hz, 1 H), 7.49 (d, J=1.47 Hz, 1 H), 7.57-7.73 (m, 9 H).
Sources & evidence
- ORD record
- ord-94f107680dd1400baaebb44e9c5fbcb0
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08692017B2
Reaction notes
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