Triethylamine → HCID 73336115, compound

Participants

Reaction Steps

A mixture of 2-pyrrolo[2,3-b]pyridin-1-ylacetic acid (51.2 mg, 0.24 mmol), 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (50.3 mg, 0.29 mmol), triethyl amine (200 μL, 1.4 mmol), and HATU (110.7 mg, 0.29 mmol) in DMF (1 mL) was stirred at room temperature for 2 hours. The reaction mixture was then diluted with 10 mL of aqueous saturated sodium bicarbonate, and extracted with EtOAc (2×15 mL). The combined organic layers were then washed with water (2×20 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 70% ethyl acetate in hexanes) to afford the desired product (25.9 mg, 0.07 mmol, 28%). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 0.8H), 8.30 (dd, J=4.8, 1.6 Hz, 1H), 7.94 (dd, J=7.2, 1.6 Hz, 1H), 7.81 (s, 0.2H), 7.45 (m, 2H), 7.36 (d, J=3.6 Hz, 0.8H), 7.31 (d, J=3.6 Hz, 0.2H), 7.18 (m, 2H), 7.09 (dd, J=7.6, 4.8 Hz, 1H), 6.58 (d, J=3.6 Hz, 1H), 5.44 (s, 0.2H), 5.32 (s, 0.8H), 3.91 (m, 2H), 2.84 (m, 2H), 2.07 (m, 2H); MS: (ES) m/z calculated for C21H18FN5O [M+H]+ 376.1, found 376.1.

Provenance & Evidence