Ethanol → HCID 86669264, compound

Participants

Reaction Conditions

Reaction Steps

[4-(1-Piperidinylmethyl)phenyl]boronic acid (135 mg, 0.475 mmol), 1-methylethyl[(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]methylcarbamate (for a preparation see Intermediate 40) (104 mg, 0.271 mmol), Tetrakis(triphenylphosphine)palladium(0) (15.68 mg, 0.014 mmol) and potassium carbonate (150 mg, 1.085 mmol) were placed in a round-bottomed flask with ethanol (1.8 mL) and Toluene (1.800 mL). The reaction mixture was stirred at 90° C. under N2 overnight. The brown reaction mixture was concentrated down and partitioned between EtOAc (10 mL) and water (10 mL). Further EtOAc (15 mL) was used to extract the product from the aqueous layer and the organics were combined, washed with saturated sodium bicarbonate solution (10 mL), dried (phase separator) and concentrated to yield a brown oil. This was purified by SP4 on a 12+M silica column using a gradient of 0.6-6% 2M methanolic ammonia in DCM. The relevant fractions were concentrated down to obtain a yellow oil (121 mg). Further purification was carried out using MDAP to give the desired compound (70 mg). LCMS (Method B): Rt=0.73, MH+=478

Provenance & Evidence