Reaktion #1181846

Reaktionsgleichung

6-bromo-naphthalene-2-carboxylic acid methyl ester

cyclopropyl boronic acid

tricyclohexylphosphine

potassium phosphate

→

title compound

Ausbeute 32.3%

6-Cyclopropylnaphthalene-2-carboxylic acid methyl ester

Ausbeute 32.3%

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed with N2 for 10 minutes
2. 2
   TemperaturAfter cooling
3. 3
   workup.ADDITIONthe reaction mixture was poured into saturated NaHCO3 solution (100 ml)
4. 4
   Extraktionextracted with EtOAc (3×50 ml)
5. 5
   WaschenThe combined organics were washed with brine (3×50 ml)
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

A flask containing 6-bromo-naphthalene-2-carboxylic acid methyl ester (1.0 g, 3.7 mmol), cyclopropyl boronic acid (421 mg, 4.9 mmol), palladium acetate (42 mg, 0.02 mmol), tricyclohexylphosphine (106 mg, 0.04 mmol) and potassium phosphate (2.802 g, 13.2 mmol) in toluene (15 ml) and water (0.75 ml) was degassed with N2 for 10 minutes. The reaction was heated at 100° C. for 1 hour. After cooling, the reaction mixture was poured into saturated NaHCO3 solution (100 ml) and extracted with EtOAc (3×50 ml). The combined organics were washed with brine (3×50 ml), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 10% EtOAc in hexane) gave the title compound (270 mg, 30%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) ppm 0.83-0.87 (2H, m), 1.05-1.11 (2H, m), 2.09-2.16 (1H, m), 3.90 (3H, s), 7.33 (1H, dd, J=8.6 Hz, 1.8 Hz), 7.70 (1H, s), 7.89-7.95 (2H, m), 8.02 (1H, d, J=8.6 Hz), 8.56 (1H, s). LC/MS: m/z not observed; retention time=3.93 min

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