Sodium Hydroxide → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-(6'-chloro-2-methyl-[3,4]bipyridinyl-3'-yl)-N-methyl-isobutyramide

HRID 347684Notes

Reaction equation

HRID 347684 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[C:11]([CH3:16])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.C([Li])CCC.[F:22][C:23]([F:41])([F:40])[C:24]1[CH:25]=[C:26]([C:34]([CH3:39])([CH3:38])[C:35](Cl)=[O:36])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1.[OH-].[Na+]>C1COCC1>[F:33][C:30]([F:31])([F:32])[C:28]1[CH:27]=[C:26]([C:34]([CH3:38])([CH3:39])[C:35]([N:8]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=2[C:10]2[C:11]([CH3:16])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])=[O:36])[CH:25]=[C:24]([C:23]([F:40])([F:22])[F:41])[CH:29]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 586946066'-Chloro-N,2-dimethyl-[3,4'-bipyridin]-3'-amineHCID 178418339Butyllithium

Product 1

HCID 210836352-(3,5-Bis-trifluoromethyl-phenyl)-N-(6'-chloro-2-methyl-[3,4]bipyridinyl-3'-yl)-N-methyl-isobutyramide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-methyl-amine in THF is added a solution of n-butyllithium in hexanes at about −78° C. After 15 min 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride is added. The reaction mixture is allowed to warm to room temperature during 30 min. After addition of an aqueous sodium hydroxide solution, the mixture is extracted with dichloromethane, dried and concentrated to give the compound 2-(3,5-Bis-trifluoromethyl-phenyl)-N-(6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-N-methyl-isobutyramide of formula II-2.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea8fb2a6a11d4830890dea7a9e4484f6
Source dataset
uspto-grants-2007_02
Patent number
US07176205B2

Reaction notes

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