Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[F:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([C:13]2[CH:14]=[CH:15][O:11][CH:12]=2)[CH:9]=1Following the same procedure used for AUP01158-1, AUP01162-1 was prepared from 2-bromo-4-fluorobenzonitrile (5.0 g, 25.0 mmol), furan-3-ylboronic acid (3.36 g, 30.0), Pd2(dba)3 (100 mg), 1,2-dimethoxyethane (25 mL) and 2M Na2CO3 (40 mL). The crude was purified by Combi flash chromatography (24 g column, 8 g silica, gradient of eluent from PE to PE/EtOac 9/1) to give the title compound as a light yellow solid. This solid had to be purified an ultimate time by drying under vacuum at 60° C. for 3 days. Finally, pure expected compound was obtained as an off white solid in 32% yield (1.47 g); mp 42-68° C. (dec.); 1H NMR (270 MHz, CDCl3) δ 6.81 (1H, d, J=2.0 Hz, ArH), 7.07 (1H, td, J=2.5 and 8.0 Hz, ArH), 7.24 (1H, dd, J=2.5 and 8.7 Hz, ArH), 7.52-7.55 (1H, m, Add), 7.72 (1H, dd, J=5.8 and 8.7 Hz, ArH), 8.06 (1H, s, ArH); HRMS (ESI) calcd. for C11H7FNO (M+H)+188.0506. found 188.0513.
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