2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → HCID 117601441, compound

HRID 578930Notes

Reaction equation

HRID 578930 reaction equation
[Cl-].[C:2]([O:6][C:7](=[O:10])[CH2:8][Zn+])([CH3:5])([CH3:4])[CH3:3].Br[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[O:20][CH3:21].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:10])=[C:13]([O:20][CH3:21])[CH:14]=1)#[N:17]

Participants

6

Reactant 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 225911814-Bromo-3-methoxybenzonitrileHCID 178451183HCID 178451183, compound

Product 1

HCID 117601441HCID 117601441, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Combined (2-(tert-butoxy)-2-oxoethyl)zinc(II) chloride (4.24 mL, 2.122 mmol) and 4-bromo-3-methoxybenzonitrile (0.30 g, 1.42 mmol) in THF (4.29 mL), then 2′-(dicyclohexylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine (0.056 g, 0.141 mmol) and Pd(dba)2 (0.041 g, 0.071 mmol) were added and the reaction was refluxed at 100° C. overnight. The reaction mixture was concentrated down by rotary evaporation and purified on a silica gel column eluting with hexanes and EtOAc to give the title compound as a yellow oil (102 mg, 29%). MS m/z [M+H]+ 248.

Workup

  1. concentrationThe reaction mixture was concentrated down by rotary evaporation
  2. custompurified on a silica gel column
  3. washeluting with hexanes and EtOAc

Sources & evidence

ORD record
ord-e50063a503a24529b43b958b8f0a6a37
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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