Reacción #1181846

Ecuación de reacción

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

cyclopropyl boronic acid

tricyclohexylphosphine

potassium phosphate

→

title compound

Rendimiento 32.3%

6-Cyclopropylnaphthalene-2-carboxylic acid methyl ester

Rendimiento 32.3%

Disolventes

toluene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed with N2 for 10 minutes
2. 2
   TemperaturaAfter cooling
3. 3
   workup.ADDITIONthe reaction mixture was poured into saturated NaHCO3 solution (100 ml)
4. 4
   Extracciónextracted with EtOAc (3×50 ml)
5. 5
   LavadoThe combined organics were washed with brine (3×50 ml)
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

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

Fuente