Potassium tert-butoxide → 4-(7-Fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-2,6-dimethyl-phenyl-3,3-dimethyl-butanamide

HRID 880679Notes

Reaction equation

HRID 880679 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].Cl.[F:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH2:16]2)=[CH:11][CH:10]=1.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:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([C:18]3[CH:9]=[C:10]([CH3:11])[C:3]([CH:29]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:28]([NH2:27])=[O:34])=[C:2]([CH3:5])[CH:1]=3)[CH2:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 450739717-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Product 1

HCID 866496304-(7-Fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-2,6-dimethyl-phenyl-3,3-dimethyl-butanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bis(dibenzylidineacetone)palladium (156 mg, 0.28 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (320 mg, 0.8 mmol) were added to dry toluene (60 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (1.9 g, 16.25 mmol), 7-fluoro-1,2,3,4-tetrahydro-isoquinoline hydrochloride salt (1.28 g, 6.8 mmol), and N-(4-bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide (5 g, 6.8 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. (1.9 g, 76%).

Workup

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

Sources & evidence

ORD record
ord-813677f834984fe8bf86d2d94cf4a390
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

Loading…