(2-(Difluoromethyl)phenyl)boronic acid → 1-[1-(4-Cyano-phenyl)-ethyl]-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

HRID 512487

Reaction equation

HRID 512487 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:13]([CH3:14])=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21](F)([F:23])[F:22])[CH:16]=3)[C:11](=[O:25])[C:10]([C:26]([OH:28])=[O:27])=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].F[CH:32](F)C1C=CC=CC=1B(O)O.BrC1C(=O)C(C(O)=O)=CN(CC2C=CC(C#N)=CC=2)C=1C.BrC1C(=O)C(C(O)=O)=CN(C(C2C=CC(C#N)=CC=2)C)C=1C>>[C:1]([C:3]1[CH:30]=[CH:29][C:6]([CH:7]([N:8]2[C:13]([CH3:14])=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([F:23])[F:22])[CH:16]=3)[C:11](=[O:25])[C:10]([C:26]([OH:28])=[O:27])=[CH:9]2)[CH3:32])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 44717243(2-(Difluoromethyl)phenyl)boronic acidHCID 867115271-(4-Cyano-benzyl)-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acidHCID 867115285-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acidHCID 867115305-Bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Product 1

HCID 867115291-[1-(4-Cyano-phenyl)-ethyl]-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Procedure

Preparation 3 is prepared following the procedure described for preparation 1d, substituting 3-(trifluoromethyl)phenylboronic acid with 2-(difluoromethyl)phenylboronic acid and substituting preparation 1c with preparation 2b as starting material. ESI mass spectrum: [M+H]+=409; Retention time HPLC: 1.00 min (Z018_S04).

Workup

  1. customPreparation 3
  2. customis prepared
  3. custom1.00 min (Z018_S04)

Sources & evidence

ORD record
ord-ee70be4464134afeb5a8e4b8bf19bd9c
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Linked notes

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