Triethylamine → HCID 57656294, compound

HRID 911660Notes

Reaction equation

HRID 911660 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:36][C:37]([CH3:41])([CH3:40])[C:38]#[CH:39]>CN(C=O)C.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I.O>[CH3:36][C:37]([CH3:41])([CH3:40])[C:38]#[C:39][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 12162Benzonitrile, 4-bromo-HCID 135123,3-Dimethyl-1-butyne

Product 1

HCID 57656294HCID 57656294, compoundYield 92%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Dissolve 4-bromobenzonitrile (3 g, 16.48 mmol) in anhydrous DMF (30 mL) in a sealed tube. Degas the solution, purge with nitrogen and add tris(dibenzylideneacetone)dipalladium(0) (453 mg, 0.49 mmol), copper(I) iodide (188 mg, 0.99 mmol), triphenylphosphine (1.08 g, 4.12 mmol), triethylamine (10 mL) and 3,3-dimethylbutyne (6.1 mL, 49.44 mmol). Heat the mixture at 90° C. overnight. Cool to room temperature, add water and extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1, 9:1) to give the desired intermediate as a solid (2.75 g, 92%).

Workup

  1. customDegas the solution
  2. custompurge with nitrogen
  3. temperatureCool to room temperature
  4. extractionextract the aqueous phase twice with EtOAc
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1, 9:1)

Sources & evidence

ORD record
ord-e727da8c649044bd8e8c957ab96603c0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…