Potassium Carbonate → (S)-tert-butyl 4-(1-amino-3-(4'-(isopropylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 1.0 g) in acetonitrile (5 mL) under nitrogen was treated with 4-fluorophenylboronic acid (0.135 g) and 4-(isopropylsulfonyl)phenylboronic acid (0.220 g) followed by aqueous potassium carbonate (2M, 1.93 mL) and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (13 mg). The mixture was stirred at 75° C. for 18 h. The reaction was evaporated, dissolved in dichloromethane, absorbed onto silica and to purified by chromatography on silica eluting with 50% ethyl acetate in isohexane and then 100% ethyl acetate to afford (S)-tert-butyl 4-(1-amino-3-(4′-fluorobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate and (S)-tert-butyl 4-(1-amino-3-(4′-(isopropylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate as a mixture (0.620 g).

Provenance & Evidence