Trifluoroacetic acid → 2-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one

Participants

Reaction Steps

To 1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide (46 mg) and 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (130 mg) in DMF (0.5 mL) was added, triethylamine (64 μL), this solution was stirred for 15 minutes then acetic acid (117 μL) was added and the solution stirred for 3 hours. Sodium triacetoxyborohydride (48 mg) in DMF (0.5 mL) was then added. The reaction mixture was stirred overnight, trifluoroacetic acid (100 μL) was added purified by HPLC to give 2-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one (1-13) as a yellow solid: 1H-NMR (500 MHz, d6 DMSO) δ 11.63 (s, 1H), 10.14 (bs, 1H), 9.06 (s, 1H), 8.41 (s, 1H), 7.51 (m, 5H), 7.35 (m, 3H), 7.26 (m, 2H), 6.70 (d, 2H, J=7.3 Hz), 6.58 (s, 1H), 6.51 (s, 1H), 4.42 (m, 2H), 4.10 (m, 2H), 3.20 (m, 2H), 2.90 (m, 2H) MS m/z (M+11) 476.

Provenance & Evidence