Diisopropylamine → HCID 59648645, compound

HRID 2105555Notes

Reaction equation

HRID 2105555 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1.C(NC(C)C)(C)C.[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[Cu]I>[C:16]1([C:22]#[C:23][C:2]2[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 10821PhenylacetyleneHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 59648645HCID 59648645, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solid mixture of 4-bromo-2-furaldehyde (1.50 g, 8.57 mmol), PdCl2(PhCN)2 (197 mg, 0.514 mmol) and CuI (65.0 mg, 0.343 mmol) was flushed under an argon stream for 1 minute (min). A solution of HP(t-butyl)3BF4 (298 mg, 1.03 mmol) and diisopropylamine (1.80 mL, 12.9 mmol) in dioxane (9 mL) was added to the solid mixture followed by phenylacetylene (1.13 mL, 10.3 mmol). The reaction was allowed to stir at room temperature (rt) under an atmosphere of argon for 15 hours (h) before being filtered through a plug of silica gel with ethyl acetate (EtOAc). The solution was then concentrated in vacuo and chromatographed over silica gel to give 4-phenylethynyl-furan-2-carbaldehyde as a colorless oil (1.54 g, 92%). Rf=0.35 (1:9 heptane/EtOAc); 1H NMR (400 MHz, CDCl3) δ ppm 9.68 (d, J=0.5 Hz, 1 H) 7.90 (s, 1 H) 7.48-7.55 (m, 2 H) 7.35-7.40 (m, 3 H) 7.33 (d, J=0.7 Hz, 1 H).

Workup

  1. customwas flushed under an argon stream for 1 minute (min)
  2. filtrationbefore being filtered through a plug of silica gel with ethyl acetate (EtOAc)
  3. concentrationThe solution was then concentrated in vacuo
  4. customchromatographed over silica gel

Sources & evidence

ORD record
ord-e519863231454a579b697cae8b78d429
Source dataset
uspto-grants-2009_08
Patent number
US07579370B2

Reaction notes

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