Triethylamine → HCID 57656020, compound

HRID 911664Notes

Reaction equation

HRID 911664 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=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:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 8171545-Bromopyridine-2-carbonitrile

Product 1

HCID 57656020HCID 57656020, compoundYield 97.8%

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 5-bromo-2-cyano-pyridine (316 mg, 1.72 mmol) in anhydrous DMF (7 mL) in a sealed tube. Degas the solution, purge with nitrogen and add tris(dibenzylideneacetone)dipalladium(0) (47 mg, 0.05 mmol), copper(I) iodide (20 mg, 0.1 mmol), triphenylphosphine (113 mg, 0.43 mmol), triethylamine (2 mL) and 3,3-dimethylbutyne (0.64 mL, 5.16 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) to give the desired intermediate as a solid (310 mg, 97%).

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)

Sources & evidence

ORD record
ord-788210ce3f614c4d8ff05972586f65a6
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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