2-Bromoethyl methyl ether → HCID 71231959, compound

Participants

Reaction Steps

tert-Butyl 3-(5-(5-(3-methoxy-3-oxopropylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (347 mg, 0.566 mmol) was dissolved in THF (5 mL) and potassium 2-methylpropan-2-olate (1699 μL, 1.70 mmol) was added. The reaction was stirred for 5 minutes. 1-Bromo-2-methoxyethane (53.2 μL, 0.566 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. The reaction was partitioned between saturated aqueous NH4Cl and CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (100% EtOAc) to afford tert-butyl 3-(5-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (256 mg, 0.438 mmol, 77.3% yield) as a white solid.

Provenance & Evidence