Sodium Carbonate → HCID 68291018, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.110 g, 0.434 mmol), 5-bromopyrimidine (0.090 g, 0.56 mmol), 1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) DCM complex (23 mg, 0.028 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1.06 mmol). The microwave vial was heated at 150° C. for 15 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHCO3 solution (15 mL). The organic layer was washed with a saturated aqueous NaHCO3 solution (15 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 20% ethyl acetate in CH2Cl2. The product band was recovered and stirred with 2% MeOH in ethyl acetate/CH2Cl2 (v/v; 1:5) (20 mL). The silica was removed by filtration, washed with ethyl acetate/CH2Cl2 (v/v; 1:1) (2×5 mL) and acetone (3×4 mL) to give the title compound as a white solid (0.075 g, 84%). 1H-NMR (500 MHz, DMSO-d6) 5.72 (s, 2H), 6.91 (d, J=8.4, 1H), 7.51 (dd, J=2.2, 8.3 Hz, 1H), 7.72 (d, J=2.2 Hz, 1H), 9.04, 9.05 (2×s, 3H).

Provenance & Evidence