4-Chloro-3-(trifluoromethyl)benzeneboronic acid → 2-(4'-Chloro-5-hydroxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13]([O:15]S(C(F)(F)F)(=O)=O)[CH:12]=[C:11](OCC2C=CC=CC=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7].[Cl:32][C:33]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:10]=[C:11]([C:36]2[CH:35]=[CH:34][C:33]([Cl:32])=[C:38]([C:39]([F:42])([F:41])[F:40])[CH:37]=2)[CH:12]=[C:13]([OH:15])[CH:14]=1)[CH2:5][CH:6]([CH3:7])[CH3:8]Participants
3
Procedure
The title compound was prepared in 70% yield from 2-(3-benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl ester (prepared in Example 15, step (d)) under the conditions described in Example 15 step (e-f) using 4-chloro-5-trifluoromethylphenylboronic acid in step (e). 1H-NMR (400 MHz, CDCl3): δ 7.84 (s, 1H), 7.65 (d, 1H), 7.55 (d, 1H), 7.04 (s, 1H), 6.92 (m, 1H), 6.86 (m, 1H), 4.98 (br s, 1H), 3.68 (m, 4H), 1.97 (m, 1H), 1.68 (m, 1H), 1.49 (m, 1H), 0.92 (d, 6H); Mass Spectrum (m/z, ESI) 399 (M−H)
Sources & evidence
- ORD record
- ord-acae64aef2cc41e988f60e3ed9e918f3
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557244B2
Reaction notes
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