Triethylamine → HCID 53663791, Verbindung

HRID 1585930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585930
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]([C:10]#[N:11])=[CH:8][CH:9]=1)=[O:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 53919960HCID 53919960, Verbindung

Produkt 1

HCID 53663791HCID 53663791, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

4-Cyano-3-(trifluoromethanesulfonyloxy)-benzoic acid methyl ester from step 1 (2.5 g, 8.1 mmol) and phenylboronic acid (2 g, 16.2 mmol) were dissolved in DMF (33 ml) and treated with Et3N (3.1 ml, 17.8 mmol). Argon was bubbled into the solution for 20 min. and then a catalytic amount of PdCl2 (PPh3)2 (285 mg, 0.405 mmol) was added. The reaction mixture was warmed to 90° C. and stirred for 3 hours under argon atmosphere. The reaction was quenched with satd. NaHCO3 (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (10% EtOAc/Hexane) to yield the desired product. FAB MS: 238 m/z (M+ +H)

Aufarbeitung

  1. customArgon was bubbled into the solution for 20 min.
  2. customThe reaction was quenched with satd
  3. extractionNaHCO3 (20 mL) and extracted with EtOAc (2×20 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-aa86365782934c3483a7fdc56a26b985
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939439

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