Potassium Carbonate → 5-(3-Difluoromethyl-phenyl)-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

HRID 524330

反応式

Br[C:2]1[C:3](=[O:15])[C:4]([C:12]([OH:14])=[O:13])=[CH:5][N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=1[CH3:8].[F:16][CH:17]([F:27])[C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CO>[F:16][CH:17]([F:27])[C:18]1[CH:23]=[C:22]([C:2]2[C:3](=[O:15])[C:4]([C:12]([OH:14])=[O:13])=[CH:5][N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=2[CH3:8])[CH:21]=[CH:20][CH:19]=1

参加物

反応条件

温度: 75 °C

実験手順

A mixture of 5-bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 3c, 3.00 g, 8.32 mmol, based on 76% purity), 3-(difluoromethyl)-phenylboronic acid (2.30 g, 13 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (690 mg, 0.94 mmol) and 2 M aqueous K2CO3 solution (10 mL, 20 mmol) in acetonitrile (20 mL) is heated for 2 h at 75° C. The reaction mixture is diluted with methanol and purified by preparative reversed phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 30° C.). Yield: 1.46 g (55% of theory); ESI mass spectrum: [M+H]+=322; Retention time HPLC: 0.92 min (Z018_S04).

後処理

custompurified by preparative reversed phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 30° C.)
custom0.92 min (Z018_S04)

出典と根拠

ORDレコード: ord-f04d5d04202f4e45ac962532a0c97e89
出典データセット: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09340507B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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