Potassium Carbonate → HCID 86711543, compound

HRID 512505Notes

Reaction equation

HRID 512505 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:11](=[O:12])[C:10](Br)=[C:9]([CH3:14])[N:8]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH3:16])[CH:7]=1)=[O:5])[CH3:2].[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CO>[CH2:1]([NH:3][C:4]([C:6]1[C:11](=[O:12])[C:10]([C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:37])([F:36])[F:25])[CH:32]=2)=[C:9]([CH3:14])[N:8]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH3:16])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 86711544HCID 86711544, compound

Product 1

HCID 86711543HCID 86711543, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid ethylamide (preparation 10, 50 mg, 0.129 mmol), 3-trifluoromethyl-phenylboronic acid (29 mg, 0.155 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (9 mg, 0.012 mmol) in acetonitrile (1 mL) is added 2 M aqueous K2CO3 solution (0.20 mL, 0.40 mmol). After stirring for 24 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: 56 mg (96% of theory); ESI mass spectrum: [M+H]+=454; Retention time HPLC: 0.93 min (Z011_S03).

Workup

  1. custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1% NH4OH, 60° C.)
  2. custom0.93 min (Z011_S03)

Sources & evidence

ORD record
ord-438443f96d53487281824ff43262eae0
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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