3-(Ethoxycarbonyl)-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 5-{4-Chloro-3-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-2-fluoro-benzoic acid ethyl ester

HRID 1096010

Reaction equation

HRID 1096010 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]([CH3:24])[C:10]([C:16]1[CH:17]=[CH:18][C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][C:27]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.N1C=CC=CC=1>[CH2:38]([O:37][C:35](=[O:36])[C:27]1[CH:28]=[C:29]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH:9]([CH3:24])[C:10]([OH:15])([C:16]3[CH:17]=[CH:18][C:19](=[O:23])[N:20]([CH3:22])[CH:21]=3)[C:11]([F:13])([F:14])[F:12])[CH:4]=2)[CH:30]=[CH:31][C:26]=1[F:25])[CH3:39]

Participants

5

Reactant 2

HCID 249017713-(Ethoxycarbonyl)-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 667825925-[2-(2-Chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 666991695-{4-Chloro-3-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-2-fluoro-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

In analogy to Example 151, step 8, 5-[2-(2-chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one (Example 189, step 5) was reacted with 4-fluoro-3-ethoxycarbonylphenylboronic acid, copper-(II)-acetate and pyridine to give the title compound as a colorless foam. MS (m/e)=528.2 [M+H+].

Sources & evidence

ORD record
ord-283ac2fa71514dbe90781c8ffd45ff81
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Linked notes

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