Triethylamine → HCID 21103208, compound

Participants

Reaction Steps

To a solution of 4-(3-phenyl-1,8-naphthyridin-2-yl)benzoic acid (9-1) (100 mg, 0.31 mmole) in dry THF (1.5 mL) was added Et3N (0.056 mL, 0.4 mmole) then isobutyl chloroformate (0.048 mL, 0.37 mmole) at 0° C. After 30 min the mixture was warmed to RT. After 30 min NaBH4 (35 mg, 0.92 mmole) was added then MeOH (1 mL) very slowly (vigorous gas evolution). After 1 hr the mixture was diluted with H2O. The pH was adjusted to 7 and the mixture extracted with CH2Cl2 (5×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The reaction was repeated using 320 mg 4-(3-phenyl-1,8-naphthyridin-2-yl)benzoic acid (9-1). After work-up the crude products were combined then purified by flash column chromatography (gradient, 0–5% MeOH/CH2Cl2) to give the title compound as a yellow foam (9-2): 1H-NMR (500 MHz, CDCl3) δ 9.14 (m, 1 H), 8.24 (m, 1 H), 8.19 (s, 1 H), 7.55 (d, J=7.81 Hz, 2 H), 7.51 (m, 1 H), 7.33 (m, 3 H), 7.27 (m, 4 H), 4.70 (s, 2 H).

Provenance & Evidence