Triethylamine → HCID 59490448, compound

Participants

Reaction Steps

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.125 g, 0.425 mmol) in dichloroethane (5 mL) and Et3N (0.18 mL, 1.27 mmol) was added 3-methoxybenzaldehyde (57.3 μL, 0.467 mmol) followed by tetramethylammonium triacetoxyborohydride (0.33 g, 1.27 mmol). The reaction mixture was shaken at room temperature 56 hours followed by the addition of 1.5M NaOH (10 mL). The reaction mixture was shaken at room temperature for 1 hour. The reaction mixture was than extracted with EtOAc (30 mL). The organic layer was washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a residue. The crude product was purified using flash column chromatography (SiO2, gradient from 50% EtOAc in hexanes to 66% EtOAc in hexane) to give the desired product, 3,7-bis(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a pale yellow solid (0.119 g, 67%). M.p.=105-107° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.25 (s, 1H), 8.11 (s, 1H), 7.28 (d, J=8.4 hz, 2H), 7.17 (d, J=8 Hz, 2H), 6.91 (d, J=8 Hz, 2H), 6.83 (d, J=8.8 hz, 2H), 5.56 (s, 2H), 3.75 (s, 3H), 3.69 (s, 3H), 3.68-3.6 (m, 4H), 3.12-3.03 (m, 2H), 2.82-2.73 (m, 2H); LCMS [M+H]: 415.

Provenance & Evidence