Piperidine → HCID 59375150, compound

Participants

Reaction Steps

Step 2 A suspension of 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-formyl-9H-carbazole-1-carboxamide (30 mg, 0.064 mmol) in THF (3 mL) was treated with piperidine (16.46 mg, 0.193 mmol) and sodium triacetoxyborohydride (34.1 mg, 0.161 mmol). The mixture was stirred at rt for 3.5 h, the was treated again with additional piperidine (16.5 mg, 0.193 mmol) and sodium triacetoxyborohydride (20 mg). After stirring overnight, the mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was purified by preparative HPLC to provide 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(piperidin-1-ylmethyl)-9H-carbazole-1-carboxamide (14 mg, 39%). 1H NMR (400 MHz, methanol-d4) δ 8.06 (2 H, dd, J=8.7, 5.4 Hz), 7.98 (1 H, d, J=7.8 Hz), 7.63 (1 H, s), 7.52 (1 H, d, J=7.3 Hz), 7.44 (1 H, t, J=7.8 Hz), 7.18-7.31 (3 H, m), 7.07 (2 H, d, J=7.5 Hz), 6.96-7.02 (1 H, m), 3.96 (2 H, s), 2.72-2.88 (4 H, m), 1.99 (3 H, s), 1.63-1.75 (4 H, m), 1.48-1.60 (2 H, m). Mass spectrum m/z 535.2 (M+H)+.

Provenance & Evidence