Sodium hydride → [4-(6-Carbamoylpyridin-3-yloxy)benzyl]phenethylcarbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve (4-hydroxybenzyl)phenethylcarbamic acid tert-butyl ester (0.0915 g, 0.279 mol) in DMF (0.090 mL). Add NaH (80% in mineral oil) (0.0092 g, 0.307 mmol). Stir for 30 minutes before adding 5-fluoropyridine-2-carboxamide (0.0391 g, 0.279 mmol). Heat at 80° C. for 3 days. Load the reaction mixture directly onto a flash 40 column and elute with 35% ethyl acetate, 3% 2.0 M NH3 in methanol and 62% hexanes to give the title compound (0.103 g, 82.4%): MS ES+ 448.5 (M+H)+, base peak ES+ 392.3 (M+2H—C(CH3)3); HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 5-95% over 19 min, 95% over 19.01-25 min], tR=19.5 min, 100% purity.

Provenance & Evidence