Diethylamine → HCID 9990663, compound

HRID 1588715Notes

Reaction equation

HRID 1588715 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:9]([CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12])#[CH:10].C(NCC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[N:6]1[CH:7]=[CH:8][C:3]([C:10]#[C:9][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 20155alpha-EthynylbenzenemethanolHCID 881004-Bromopyridinium chloride

Product 1

HCID 9990663HCID 9990663, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Place 4-bromopyridine hydrochloride (2.33 g, 12 mmol), α-(ethynyl)-benzenemethanol (1.95 g, 14.8 mmol) and diethylamine (25 mL) under nitrogen atmosphere. Add bis(triphenylphosphine)palladium(II) chloride (105 mg) then copper(I) iodide (59 mg). Stir at room temperature for 3 hours. Evaporate the solvent in vacuo, stir the residue in ethyl acetate (50 mL) and filter the solids. Evaporate the solvent in vacuo and purify by silica gel chromatography (4:3 ethyl acetate/hexane) to yield 0.4 g. Recrystallize (hexane/chloroform) to yield 0.2 g of the title compound; mp 93°-96° C.

Workup

  1. customEvaporate the solvent in vacuo
  2. stirringstir the residue in ethyl acetate (50 mL)
  3. filtrationfilter the solids
  4. customEvaporate the solvent in vacuo
  5. custompurify by silica gel chromatography (4:3 ethyl acetate/hexane)
  6. customto yield 0.4 g
  7. customRecrystallize (hexane/chloroform)

Sources & evidence

ORD record
ord-0e099d04ab2241488b7302d1e62de669
Source dataset
uspto-grants-1993_06
Patent number
US05223518

Reaction notes

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