Sodium Iodide → HCID 178508235, compound

Participants

Reaction Steps

A suspension of (S)-3-(2-fluoropyridin-4-yl)-7-(2-methoxypyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.075 g, 0.17 mmol, prepared as described in BB41 and AA1 using 2-methoxypyridin-3-ylboronic acid and 2-fluoropyridin-4-ylboronic acid) and sodium iodide, anhydrous (0.077 g, 0.51 mmol) in acetonitrile (6.0 mL) was treated chlorotrimethylsilane (0.070 mL, 0.55 mmol) and the resulting mixture was stirred at room temperature for 16 h. The reaction was concentrated to dryness on the rotary evaporator, the resulting residue was taken up in dichloromethane (25 mL), water (15 mL), and formation of insoluble solids was observed. The solids were collected by filtration. The solid was dissolved in DMSO (1.5 mL) and loaded on the AGILENT MASS-TRIGGERRED HPLC system for purification using a MeCN/Water/0.1% TFA gradient and PHENOMENEX Gemini Axia-5 C-18 column (150×30 mm). The solvent was removed from the pure fractions in the GENEVAC and the resulting product was dissolved in methanol (1.5 mL) and neutralized by passing the solution through a Polymer Lab-HCO3 Macroporous resin cartridge (0.36 mmol loading; 500 mgs), and the filtrate was concentrated under high vacuum to yield the product (S)-3-(2′-amino-3-(2-fluoropyridin-4-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazole]-7-yl)pyridin-2-ol as an amorphous off-white solid [MS: m/z=442.1 (M+H)].

Provenance & Evidence