(4-Cyano-3-fluorophenyl)boronic acid → 2-(4-Cyano-3-fluoro-4''-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-4-methyl-pentanoic acid
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.[C:35]([C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][C:38]=1[F:46])#[N:36]>>[C:35]([C:37]1[CH:42]=[CH:41][C:40]([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:39][C:38]=1[F:46])#[N:36]Participants
3
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-cyano-3-fluoro-phenylboronic acid under the conditions described in Example 1; 1H NMR (400 MHz, MeOD) δ ppm 0.88 (dd, J=6.60, 2.93 Hz, 6H), 1.46 (dt, J=13.45, 6.72 Hz, 1H), 1.66 (ddd, J=13.69, 7.21, 6.97 Hz, 1H), 1.96 (ddd, J=13.27, 7.95, 7.64 Hz, 1H), 3.78 (t, J=7.83 Hz, 1H), 7.59-7.70 (m, 6H) 7.72-7.82 (m, 4H); Calcd for C26H21F4NO2 (M+H) 456.44, Found 456.
Sources & evidence
- ORD record
- ord-02fd1f967ff248929a6f545139e4d97f
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106236B2
Reaction notes
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