Acetic Acid → HCID 67003874, compound

Participants

Reaction Steps

To a solution of 4-(5-chloro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)benzaldehyde (Example 8B) (2.10 g, 3.72 mmol) in tetrahydrofuran (33.8 mL) was added sequentially acetic acid (0.426 mL, 7.45 mmol), sodium sulfate (1.058 g, 7.45 mmol), and pyrrolidine (0.466 ml, 5.58 mmol). The reaction was stirred for 0.5 hours at ambient temperature, and sodium triacetoxyborohydride (1.578 g, 7.45 mmol) was added in a single portion. The reaction was stirred for 1 hour and was then quenched by the addition of saturated aqueous sodium bicarbonate solution (20 mL), ethyl acetate (20 mL), and solid sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with addition ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 10% methanol in dichloromethane with 1% v/v aqueous ammonium hydroxide solution, to give the title compound. MS ESI(+) m/z 619.3 [M+H]+.

Provenance & Evidence