Potassium tert-butoxide → N-[2,6-Dimethyl-4-(7-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethyl-butanamide

HRID 880696Notes

Reaction equation

HRID 880696 reaction equation
CC(C)([O-])C.[K+].Cl.[F:8][C:9]([F:21])([F:20])[C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][NH:16][CH2:17]2)=[CH:12][CH:11]=1.Br[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([NH:30][C:31](=[O:37])[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[C:25]([CH3:38])[CH:24]=1>C1(C)C=CC=CC=1>[CH3:29][C:27]1[CH:28]=[C:23]([N:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][C:10]([C:9]([F:8])([F:20])[F:21])=[CH:11][CH:12]=3)[CH2:17]2)[CH:24]=[C:25]([CH3:38])[C:26]=1[NH:30][C:31](=[O:37])[CH2:32][C:33]([CH3:35])([CH3:34])[CH3:36]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 441182867-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Product 1

HCID 58097350N-[2,6-Dimethyl-4-(7-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-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) and stirred for 15 minutes under argon. Potassium tert-butoxide (4.75 g, 42.3 mmol), 7-trifluoromethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride salt (4.82 g, 20.3 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, filtered through silica gel, and recrystallized from toluene to afford the title compound as a solid. (5.94 g, 85%).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. filtrationfiltered through silica gel
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-ef37906a337f4519b51d48ef7a0fe1a9
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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