Dimethylformamide → Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate

HRID 1472633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472633
Cl[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].CN(C=O)C>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:22]1[CH:23]=[CH:24][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:20][CH:21]=1)[C:11]([CH3:12])=[CH:10]2

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 49146642-Chloro-6-methoxy-3-methylquinoline

Produkt 1

HCID 66980055Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(methoxycarbonyl)phenylboronic acid (184 mg, 1.02 mmol), TEA (0.35 mL, 2.41 mmol), and PdCl2(dppf) (35 mg, 0.048 mmol) was added 2 mL of DMF under argon. The mixture was then stirred for 2.5 h at 120° C. in a microwave reactor. The crude mixture was then diluted with water (25 mL) and extracted with EtOAc (25 mL×2). The organics were washed with brine (50 mL), dried over sodium sulfate, and concentrated to yield 250 mg of crude material. The crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes to yield 37 mg (25% yield) of methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate.

Aufarbeitung

  1. extractionextracted with EtOAc (25 mL×2)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield 250 mg of crude material
  6. customThe crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-01a2a0f3e5464ebeb9f40d96779a618c
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012646B2

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