Potassium tert-butoxide → N-[2,6-dimethyl-4-(2-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-phenyl]-3,3-dimethyl-butyramide

HRID 1043825

Reaction equation

HRID 1043825 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:20])([F:19])[C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][NH:14][CH2:13][CH2:12][C:11]=2[N:10]=1.Br[C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([NH:29][C:30](=[O:36])[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[C:24]([CH3:37])[CH:23]=1>C1(C)C=CC=CC=1>[CH3:28][C:26]1[CH:27]=[C:22]([N:14]2[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([C:8]([F:7])([F:19])[F:20])[CH:18]=[CH:17][C:16]=3[CH2:15]2)[CH:23]=[C:24]([CH3:37])[C:25]=1[NH:29][C:30](=[O:36])[CH2:31][C:32]([CH3:34])([CH3:33])[CH3:35]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 534719842-(Trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridineHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Product 1

HCID 25182406N-[2,6-dimethyl-4-(2-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-phenyl]-3,3-dimethyl-butyramide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bis(dibenzylidineacetone)palladium (15 mg, 0.026 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (40 mg, 0.1 mmol) were added to dry toluene (5 mL purged with argon for 30 min), and the mixture was stirred for an additional 30 minutes at room temperature under argon. Potassium tert-butoxide (188 g, 71 mmol), compound 7 (191 mg, 0.8 mmol), aid compound 8 (200 mg, 0.67 mmol) were then added; the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then cooled to room temperature, filtered through a pad of silica gel, and purified by preparative TLC (DCM/MeOH 5%) to afford compound 11.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered through a pad of silica gel
  4. custompurified by preparative TLC (DCM/MeOH 5%)

Sources & evidence

ORD record
ord-730be7c5478a4503a4fd7465552b4cb8
Source dataset
uspto-grants-2013_10
Patent number
US08563566B2

Linked notes

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