Diethylamine → HCID 11447136, compound

HRID 1588719Notes

Reaction equation

HRID 1588719 reaction equation
Cl.Br[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=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:5]1[CH:6]=[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]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 20155alpha-EthynylbenzenemethanolHCID 5221743-Bromopyridine hydrochloride

Product 1

HCID 11447136HCID 11447136, compound

Reagents, catalysts & solvents 2

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

Procedure

Place 3-bromopyridine hydrochloride (0.78 g, 4 mmol), α-(ethynyl)-benzenemethanol (661 mg, 5 mmol) and diethylamine (25mL) under nitrogen atmosphere. Add bis(triphenyl-phosphine)palladium(II) chloride (140mg) then copper(I) iodide (20 mg). Stir overnight at room temperature and filter. Evaporate the solvent in vacuo and filter through silica gel (2:1 ethyl acetate/hexane). Evaporate the solvent in vacuo and recrystallize (25% ethyl acetate/hexane) to yield the title compound.

Workup

  1. filtrationfilter
  2. customEvaporate the solvent in vacuo
  3. filtrationfilter through silica gel (2:1 ethyl acetate/hexane)
  4. customEvaporate the solvent in vacuo
  5. customrecrystallize (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-716b65aab9554872a0a2134142731550
Source dataset
uspto-grants-1993_06
Patent number
US05223518

Reaction notes

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