3-Cyano-4-fluorophenylboronic acid → HCID 59004792, compound

HRID 426331Notes

Reaction equation

HRID 426331 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:38]=[C:39](B(O)O)[CH:40]=[CH:41][C:42]=1[F:43])#[N:36]>>[C:35]([C:37]1[CH:38]=[C:39]([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:40]=[CH:41][C:42]=1[F:43])#[N:36]

Participants

3

Reactant 2

HCID 27579643-Cyano-4-fluorophenylboronic acidHCID 577550554-Methyl-2-(5-trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 59004792HCID 59004792, compound

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 3-cyano-4-fluoro-phenylboronic acid under the conditions described in Example 1; 1H NMR (400 MHz, MeOD) δ ppm 0.87 (dd, J=6.48, 2.81 Hz, 6H), 1.47 (dt, J=13.39, 6.63 Hz, 1H), 1.65 (ddd, J=13.63, 7.09, 6.91 Hz, 1H), 1.92-2.00 (m, 1H), 3.71-3.77 (m, 1H), 7.54 (td, J=7.70, 1.47 Hz, 1H), 7.59-7.61 (m, 1H), 7.65-7.72 (m, 3H), 7.77-7.81 (m, 2H), 7.86-7.89 (m, 1H), 7.96 (ddd, J=8.80, 5.14, 2.45 Hz, 1H), 8.02 (dd, J=5.99, 2.32 Hz, 1H); Calcd for C26H21F4NO2 (M+H) 456.44, Found 456.

Sources & evidence

ORD record
ord-7c6ba65adb794449878cb85fbe0fe02d
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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