1,3-Dichloroacetone → 6-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine

HRID 322294

반응식

HRID 322294 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Cl:9][CH2:10][C:11]([CH2:13]Cl)=O>COCCOC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:13]=[C:11]([CH2:10][Cl:9])[N:1]=2)[CH:4]=1

참가 물질

4

반응물 2

HCID 107931,3-DichloroacetoneHCID 706222-Amino-5-bromopyridine

생성물 1

HCID 116228946-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine수율 10.4%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 2-amino-5-bromopyridine (10.0 g). 1,3-dichloroacetone (7.71 g) and 1,2-dimethoxyethane (40 ml) was stirred at room temperature for 4 hours. The precipitated crystals were collected by filtration, to which ethanol (100 ml) was added and heated under reflux. The reaction mixture was concentrated, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give crystals of 6-bromo-2-chloromethylimidazo-[1,2-a]pyridine (1.48 g, 10%). Recrystallization from ethyl acetate-hexane gave colorless needles, mp 129-130° C.

후처리

  1. filtrationThe precipitated crystals were collected by filtration, to which ethanol (100 ml)
  2. additionwas added
  3. temperatureheated
  4. temperatureunder reflux
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fb4cf1708f384c6ea2674a91b781cbde
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

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