Diethylamine → HCID 11447136, compound

HRID 1654767Notes

Reaction equation

HRID 1654767 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 (25 mL) under nitrogen atmosphere. Add bis(triphenylphosphine)palladium(II) chloride (140 mg) 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-e035492464a04b19a0f0504955336aba
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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