Sodium hydride → HCID 69130062, compound

Participants

Reaction Conditions

Reaction Steps

Suspend sodium hydride (138 mg, 5.46 mmol) in tetrahydrofuran (6 mL) and cool to 0° C. in an ice bath. Add (2-mercaptoethyl)carbamic acid tert-butyl ester (0.461 mL, 2.73 mmol) dropwise over 5 minutes. Stir reaction for 30 minutes, add 2,6-difluoropyridine (0.495 mL, 0.546 mmol), remove ice bath and stir an additional hour. Re-cool reaction and quench with water. Extract with 1/1 hexanes/ethyl acetate. Dry organics over magnesium sulfate, filter and evaporate. Perform flash column chromatography (ethyl acetate/hexanes). Dissolve resulting orange oil in trifluoroacetic acid (3 mL) and stir for 15 minutes. Concentrate the reaction with a stream of dry nitrogen, re-dissolve in dry methylene chloride and evaporate to give 120 mg of the title compound as an orange oil. 1H NMR (d MeOH): 7.70 (m, 1H), 7.22 (m, 1H), 6.78 (m, 1H), 3.44 (m, 2H), 3.34 (m, 2H).

Provenance & Evidence