Triethylamine → 2-(6-Isocyano-2,7-naphthyridin-1-yl)isoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

4-8 (90.0 mg, 0.280 mmol) was suspended in CH2Cl2 (10 mL) and cooled to 0° C. To the mixture were added triphosgene (252 mg, 0.85 mmol) followed by Et3N (0.240 mL, 1.69 mmol). The mixture was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2, washed with saturated aqueous NaHCO3, brine, and dried over Na2SO4. The residue was purified by silica gel chromatography (0-5% EtOAc in CH2Cl2) to give 73.3 mg (41%) of 4-9 as a pale white solid: 1H NMR (300 MHz, CDCl3) δ 9.18 (1H, br s), 8.86 (1H, d, J=5.7 Hz), 8.06 (2H, m), 7.90 (2H, m), 7.85 (1H, br s), 7.84 (1H, d, J=5.7 Hz); ESI-MS m/z 301 [C17H8N4O2+H]+.

Provenance & Evidence