3-(Dimethylamino)benzeneboronic acid → HCID 59004761, compound

HRID 426366Notes

Reaction equation

HRID 426366 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.[CH3:35][N:36]([CH3:46])[C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=1>>[CH3:35][N:36]([CH3:46])[C:37]1[CH:42]=[C:41]([C:14]2[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:4]([OH:3])=[O:34])[CH:11]=[C:12]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=3)[CH:13]=2)[CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 27625273-(Dimethylamino)benzeneboronic acidHCID 577550554-Methyl-2-(5-trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 59004761HCID 59004761, 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-dimethylamino-phenylboronic acid under the conditions described in Example 1; 1H NMR (300 MHz, MeOD) δ ppm 0.99 (dd, J=6.59, 2.45 Hz, 6H), 1.58 (dt, J=13.28, 6.73 Hz, 1H), 1.78 (ddd, J=13.75, 7.16, 6.97 Hz, 1H), 2.03-2.13 (m, 1H), 3.32 (s, 6H), 3.88 (t, J=7.72 Hz, 1H), 7.49 (d, J=7.91 Hz, 1H), 7.68-7.83 (m, 7H), 7.86-7.94 (m, 3H); Calcd for C27H28F3NO2 (M+H) 456.21, Found 456.

Sources & evidence

ORD record
ord-0f5c7b45fcce48c392fbe3f8db02aaeb
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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