Hydrochloric Acid → HCID 60197936, compound

Participants

Reaction Steps

2-Amino-5-fluoropyridine (34.3 mg, 0.306 mmol, 1.10 eq) was dissolved in THF (0.7 mL) in a flame-dried round bottom flask. A 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (0.613 mL, 0.306 mmol, 1.10 eq) was added dropwise and the reaction was stirred for 5 minutes. Methyl 4-(5-cyanopyridin-3-yloxy)-6-methylpicolinate (75 mg, 0.28 mmol, 1.0 eq) was added as a solution in THF (0.7 mL) and the reaction was stirred for 30 minutes. The reaction was diluted with EtOAc, neutralized with 1N HCl, and washed with water. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 45 mg (46%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.48 (s, 1H), 8.99 (s, 1H), 8.87 (d, J=2.4 Hz, 1H), 8.41-8.39 (m, 2H), 8.27 (dd, J=9.1, 4.1 Hz, 1H), 7.86 (td, J=8.7, 2.8 Hz, 1H), 7.56 (d, J=1.7 Hz, 1H), 7.28 (d, J=1.7 Hz, 1H), 2.58 (s, 3H); [M+1]+: 350.2.

Provenance & Evidence