1,2,3,4-Tetrahydroisoquinoline → HCID 24936951, compound

HRID 2067780Notes

Reaction equation

HRID 2067780 reaction equation
CC(C)([O-])C.[K+].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1.Br[C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([NH:25][C:26](=[O:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:20]([CH3:33])[CH:19]=1>C1(C)C=CC=CC=1>[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([NH:25][C:26](=[O:32])[CH2:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[C:20]([CH3:33])[CH:19]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 23665647Potassium tert-butoxideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Product 1

HCID 24936951HCID 24936951, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (150 mg, 1.34 mmol), 1,2,3,4-tetrahydroisoquinoline (107 mg, 0.8 mmol) and N-(4-bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide (200 mg, 0.67 mmol) were then added, and the reaction mixture was stirred at 90° C. overnight. The reaction mixture was then cooled to room temperature, concentrated, and purified by thin layer chromatography (dichloromethane:methanol 5%) to afford the title compound as a solid. (113.20 mg, 50%).

Workup

  1. stirringthe reaction mixture was stirred at 90° C. overnight
  2. concentrationconcentrated
  3. custompurified by thin layer chromatography (dichloromethane:methanol 5%)

Sources & evidence

ORD record
ord-a1d289fc25054b4e99dfdba1dbbbb2d5
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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