6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride → HCID 24937078, compound

HRID 2067792Notes

Reaction equation

HRID 2067792 reaction equation
CC(C)([O-])C.[K+].Cl.[F:8][C:9]([F:21])([F:20])[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][NH:15][CH2:14][CH2:13]2.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:15]2[CH2:14][CH2:13][C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:9]([F:8])([F:20])[F:21])[CH:11]=3)[CH2:16]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 217125586-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 23665647Potassium tert-butoxideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Product 1

HCID 24937078HCID 24937078, compound

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 30 minutes under argon. Potassium tert-butoxide (4.75 mg, 42.3 mmol), 6-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 and recrystallized from toluene to afford the title compound as a solid. (5.55 g, 79%).

Workup

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

Sources & evidence

ORD record
ord-7efbe403c9eb414c9572d0dc021e7d80
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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