N-bromobutanimide → 8-Chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine

25.2 g of the compound [67-1] was dissolved in a mixed solvent of 320 mL of 1,4-dioxane and 32 mL of water. Then, 22.2 g of N-bromosuccinic acid imide was added under an ice-cold condition, and the mixture was stirred at room temperature for 2 hours. To the reaction solution, 16.0 g of 2-amino-3-chloropyridine was added, and the mixture was stirred overnight at room temperature. A saturated aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with a mixed solvent of chloroform and methanol (mixing ratio: 9/1). The obtained organic layer was dried over anhydrous sodium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. To the obtained residue, hexane was added, and the mixture was stirred for 30 minutes. The solid was taken by filtration, and dried under reduced pressure to obtain 20.0 g of 8-chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine [67-2] (hereinafter, referred to as the compound [67-2]) as a yellow solid.

1. stirringthe mixture was stirred overnight at room temperature
2. extractionthe mixture was extracted with a mixed solvent of chloroform and methanol (mixing ratio: 9/1)
3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
4. filtrationThe insolubles were filtered
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionTo the obtained residue, hexane was added
7. stirringthe mixture was stirred for 30 minutes
8. filtrationThe solid was taken by filtration
9. customdried under reduced pressure

ORD record

ord-7bc627f47c6e4ac3a5c8534d4c5dca3d

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2