3-(Trifluoromethyl)phenylboronic acid → 5-Fluoro-6-(2-hydroxy-ethoxy)-3'-trifluoromethyl-biphenyl-3-carboxylic acid
Reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:12][CH2:13][O:14]C(=O)C)=[C:6](Br)[CH:5]=1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>>[F:10][C:8]1[CH:9]=[C:4]([C:3]([OH:2])=[O:19])[CH:5]=[C:6]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([C:21]([F:32])([F:31])[F:20])[CH:27]=2)[C:7]=1[O:11][CH2:12][CH2:13][OH:14]Participants
3
Procedure
The compound of step 1 was coupled to 3-trifluoromethyl-phenylboronic acid in analogy to step 3 of example 92, and the obtained ester intermediate was hydrolyzed in analogy to step 4 of example 1 to yield 5-fluoro-6-(2-hydroxy-ethoxy)-3′-trifluoromethyl-biphenyl-3-carboxylic acid. This intermediate was coupled to the compound of step 1 of example 355 in analogy to step 1 of example 3, and the obtained ester intermediate hydrolyzed in analogy to step 4 of example 1 to yield the title compound.
Sources & evidence
- ORD record
- ord-32bb1a909d654a15a990ebc804cf706f
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618304B2
Reaction notes
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