Diethylamine → HCID 15289377, compound

HRID 1654759Notes

Reaction equation

HRID 1654759 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:9][N:10]([CH3:21])[C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:19]#[CH:20])[OH:18])=[CH:13][CH:12]=1.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>[CH3:9][N:10]([CH3:21])[C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:19]#[C:20][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[OH:18])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 881004-Bromopyridinium chlorideHCID 2749588HCID 2749588, compound

Product 1

HCID 15289377HCID 15289377, compoundYield 49.5%

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 (0.78 g, 4 mmol), 4-dimethylamino-α-(ethynyl)-benzenemethanol (0.88 g, 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 0.5 g of the title compound; mp 117° C.

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-529e124111da4510b82d07ea432d40d8
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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