(E)-6-methoxy-hex-1-enylboronic acid → 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[(1E)-6-methoxy-hex-1-en-1-yl]-phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one

Participants

Reaction Conditions

Reaction Steps

A degassed solution of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (200 mg, 0.488 mmol) and (E)-6-methoxy-hex-1-enylboronic acid (0.537 mmol) in 1 ml of 2 M K2CO3 and 2.5 ml of DME is treated with Pd(CH3CN)2Cl2 (20 mg, 5%), the mixture heated at 95° C. under a nitrogen atmosphere for 16 h, diluted with water and extracted with CH2Cl2. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified on a silica gel cartridge and then by preparative HPLC to afford the title compound, 121 mg (56% yield), identified by NMR and mass spectral analyses. (1H-NMR 300 MHz, CDCl3): 7.49 (d, 2H); 7.42 (s br, 1H); 7.27 (m, 5H); 7.06 (d, 2H); 6.49 (dd, 1H); 6.36 (d, 1H); 6.20 (dt, 1H); 3.41 (t, 2H); 3.35 (s, 3H); 3.12 (s, 3H); 2.22 (dt, 2H); 1.69-1.47 (m, 4H). MS [M+H]+ 444.4

Provenance & Evidence