Potassium Phosphate, Tribasic → HCID 54752886, compound

Temperature

100 °C

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

1. customwas degassed with N2 for 10 minutes
2. temperatureAfter cooling
3. additionthe reaction mixture was poured into saturated NaHCO3 solution (100 ml)
4. extractionextracted with EtOAc (3×50 ml)
5. washThe combined organics were washed with brine (3×50 ml)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-929d9f37214740f6b0b33321133e3ac2

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134004B2