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Potassium Carbonate → 1-[1-(4-Cyano-phenyl)-ethyl]-2-methyl-4-oxo-2'-trifluoromethyl-1,4-dihydro-[3,4']bipyridinyl-5-carboxylic acid methylamide

HRID 512504
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HRID 512504 반응식
[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9](Br)=[C:8]([CH3:13])[N:7]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH3:15])[CH:6]=1)=[O:4].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[CH:28][N:27]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:30]2[CH:29]=[CH:28][N:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=2)=[C:8]([CH3:13])[N:7]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH3:15])[CH:6]=1)=[O:4]
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 451588802-(Trifluoromethyl)pyridine-4-boronic acidHCID 867115375-Bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid methylamide

생성물 1

HCID 867115421-[1-(4-Cyano-phenyl)-ethyl]-2-methyl-4-oxo-2'-trifluoromethyl-1,4-dihydro-[3,4']bipyridinyl-5-carboxylic acid methylamide

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 887Methanol용매
HCID 6342Acetonitrile용매

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온도
75 °C

실험 절차

To a solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid methylamide (preparation 9, 240 mg, 0.641 mmol), 2-(trifluoromethyl)pyridine-4-boronic acid (148 mg, 0.78 mmol), palladium (0) tetrakis(triphenylphosphine) (79 mg, 0.068 mmol) in acetonitrile (4 mL) is added 2 M aqueous K2CO3 solution (0.60 mL, 1.20 mmol). After stirring for 72 h at 75° C., the reaction mixture is diluted with methanol and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1% NH4OH, 60° C.). Yield: 48 mg (17% of theory); ESI mass spectrum: [M+H]+=441; Retention time HPLC: 0.78 min (Z011_S03).

후처리

  1. custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1% NH4OH, 60° C.)
  2. custom0.78 min (Z011_S03)

출처 및 근거

ORD 기록
ord-61f2845d211b476d8dcf2d2acb529b07
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102624B2

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