2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → HCID 24937078, compound

HRID 880704Notes

Reaction equation

HRID 880704 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[K+].Cl.[F:36][C:37]([F:49])([F:48])[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[CH2:44][NH:43][CH2:42][CH2:41]2.Br[C:51]1[CH:56]=[C:55]([CH3:57])[C:54]([NH:58][C:59](=[O:65])[CH2:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[C:53]([CH3:66])[CH:52]=1>C1(C)C=CC=CC=1>[CH3:57][C:55]1[CH:56]=[C:51]([N:43]2[CH2:42][CH2:41][C:40]3[C:45](=[CH:46][CH:47]=[C:38]([C:37]([F:36])([F:48])[F:49])[CH:39]=3)[CH2:44]2)[CH:52]=[C:53]([CH3:66])[C:54]=1[NH:58][C:59](=[O:65])[CH2:60][C:61]([CH3:63])([CH3:62])[CH3:64]

Participants

6

Reactant 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 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′-dicyclohexylphosphanyl-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 mg, 42.3 mmol), 6-Trifluoromethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (4.82 g, 20.3 mmol) and N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butyramide (5 g, 16.8 mmol) were then added and the reaction mixture was stirred at 80° C. over night. 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. over night
  2. customrecrystallized from toluene

Sources & evidence

ORD record
ord-3c142aeaba6f4b77ba1c5b6168a738f5
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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