Ethyl Acetate → HCID 11160141, compound

Temperature

90 °C

A mixture of bromoacetaldehyde diethyl acetal (20 mL), concentrated hydrobomic acid (5 mL) and water (20 mL) is heated at 90° C. for 1.5 h. The reaction mixture is poured into 250 mL of water and 50 g sodium bicarbonate is gradually added. 2-Amino-6-bromo-4-methylpyridine (3 g, 0.016 mol) is then added and the mixture is stirred at room temperature for 3 h. Ethyl acetate (100 mL) and water (50 mL) are added. The organic layer is separated and extracted with hydrochloric acid (1N, 3×100 mL). The combined aqueous layer is neutralized with ammonium hydroxide at 0° C. and extracted with dichloromethane (3×200 mL). The combined organic layer is dried over sodium sulfate. Evaporation of the solvent gave 5-bromo-7-methylimidazo[1,2-a]pyridine (2.95 g, 76%) as a white solid, m.p. 53-54° C.

1. concentrationconcentrated hydrobomic acid (5 mL) and water (20 mL)
2. additionThe reaction mixture is poured into 250 mL of water and 50 g sodium bicarbonate
3. additionis gradually added
4. customThe organic layer is separated
5. extractionextracted with hydrochloric acid (1N, 3×100 mL)
6. customis neutralized with ammonium hydroxide at 0° C.
7. extractionextracted with dichloromethane (3×200 mL)
8. dry with materialThe combined organic layer is dried over sodium sulfate
9. customEvaporation of the solvent

ORD record

ord-9023da4e57934a7d9f5e9d2684581fe2

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723332B2