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General procedure: (a) Alkylation and Suzuki coupling in one pot: A mixture of 0.58 mmol of halogen derivative 23 or 24, 100 mg (0.72 mmol, 1.2 equiv) of K2CO3 and 3 mL of DMF was stirred in a 100 C oil bath for 30 min, cooled to rt, and treated with alkylating reagent (1.2 equiv to halogen derivative). The resulting mixture was subjected to microwave reactor at 110 C for 10,000 s, cooled to rt, charged with a mixture of boronic acid (1.2 equiv to halogen derivative), 115 mg of K2CO3 (1.2 equiv to boronic acid), and 15 mg of PdCl2, and again subjected to microwave reactor at 130 C for 35 min. The resulting suspension was evaporated to dryness. The residue was adsorbed on silica gel and purified by standard flash chromatography method with MeOH and DCM to give the crude product (bearing protected and unprotected hydroxyls) as a mixture.
2-((2-amino-5-bromopyridin-3-yl)oxy)ethyl acetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
97%
In a 40 mL reaction vial under nitrogen gas, was added (1977) <strong>[39903-01-0]2-amino-5-bromopyridin-3-ol</strong> (0.320 g, 1.693 mmol) and DMF (5 mL). The mixture was cooled to 5 °C and NaH (0.102 g, 2.54 mmol) was added. The reaction mixture was stirred at 5 °C for 1 hour. Next, 2-bromoethyl acetate (0.283 mL, 2.54 mmol) was introduced neat via a syringe. The reaction mixture was stirred at 5 °C and slowly warmed to room temperature overnight. The mixture was cooled to 5 °C and carefully diluted with water. Ethyl acetate was added and the mixture was transferred to a separatory funnel. The layers were separated and the organics were washed with brine, dried over sodium sulfate, filtered and concentrated to afford (1978) 2-((2-amino-5-bromopyridin-3-yl)oxy)ethyl acetate as a tan oil (0.45 g, 97percent). LC-MS: M+1= 275/277, rt = 0.52 min, [Al].
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