3-Difluoromethyl-phenylboronic acid → (S)-5-(3-Difluoromethyl-phenyl)-1-(2-methoxy-1-methyl-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 524354Notes

Reaction equation

HRID 524354 reaction equation
[CH3:1][S:2]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17](Br)=[C:16]([CH3:21])[N:15]([C@@H:22]([CH3:26])[CH2:23][O:24][CH3:25])[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:29][CH:30]([F:40])[C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1>>[CH3:1][S:2]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:30]([F:40])[F:29])[CH:36]=3)=[C:16]([CH3:21])[N:15]([C@@H:22]([CH3:26])[CH2:23][O:24][CH3:25])[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 447172443-Difluoromethyl-phenylboronic acidHCID 86711605(S)-5-Bromo-1-(2-methoxy-1-methyl-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

Product 1

HCID 86711604(S)-5-(3-Difluoromethyl-phenyl)-1-(2-methoxy-1-methyl-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

Procedure

Example 42 is prepared following the procedure for Example 24.1, substituting preparation 24 with preparation 41c and replacing 3-(trifluoromethyl)phenylboronic acid with 3-(difluoromethyl)phenylboronic acid. ESI mass spectrum: [M+H]+=519; Retention time HPLC: 0.97 min (Z018_S04).

Workup

  1. customExample 42 is prepared
  2. custompreparation 24
  3. custom0.97 min (Z018_S04)

Sources & evidence

ORD record
ord-a2cbbc09e02d4ebd8a66bce5c08510db
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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