Potassium tert-butoxide → 4-(6-Fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-2,6-dimethylphenyl-3,3-dimethyl butanamide

HRID 880676

Reaction equation

HRID 880676 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].Cl.[F:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12]2.BrC1C=C(C)C([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=C(C)C=1>C1(C)C=CC=CC=1>[F:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([C:10]1[CH:9]=[C:18]([CH3:17])[C:3]([CH:29]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:28]([NH2:27])=[O:34])=[C:2]([CH3:5])[CH:1]=1)[CH2:13][CH2:12]2

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 450740426-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Product 1

HCID 866496284-(6-Fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-2,6-dimethylphenyl-3,3-dimethyl butanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bis(dibenzylidineacetone)palladium (390 mg, 0.68 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (800 mg, 2.0 mmol) were added to dry toluene (150 mL purged with argon for 30 minutes) and stirred for 30 minutes under argon. Potassium tert-butoxide (4.75 mg, 42.3 mmol), 6-fluoro-1,2,3,4-tetrahydro-isoquinoline hydrochloride salt (3.2 g, 17.0 mmol), and N-(4-bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide (5 g, 16.8 mmol) were then added, and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then cooled to room temperature and recrystallized from toluene to afford the title compound as a solid. (5.11 g, 83%).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. customrecrystallized from toluene

Sources & evidence

ORD record
ord-2465b035f16a400ebdefc9548d845fee
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Linked notes

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