4-Fluorobenzoic Acid → 5Chloro-2-(4fluorophenyl)imidazo[4,5-b]pyridine

HRID 396369노트

반응식

HRID 396369 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=1>>[Cl:9][C:4]1[N:3]=[C:2]2[N:1]=[C:15]([C:14]3[CH:18]=[CH:19][C:11]([F:10])=[CH:12][CH:13]=3)[NH:8][C:7]2=[CH:6][CH:5]=1

참가 물질

3

반응물 2

HCID 99734-Fluorobenzoic AcidHCID 106306156-Chloropyridine-2,3-diamine

생성물 1

HCID 224861255Chloro-2-(4fluorophenyl)imidazo[4,5-b]pyridine수율 46.6%

실험 절차

2,3-Diamino-6-chloropyridine (Davos-Bulk supplier, 2.25 g 15.6 mmol) and 4-fluorobenzoic acid (2.62 g 18.7 mmol) are treated with polyphosphoric acid (56.4 g) at 150° C. for 6 h. The reaction mixture is poured on ice-water/NH3conc. and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to yield the crude product, which is purified by recrystallisation from ethyl acetate/tert.butyl methyl ether to yield the title compound (1.8 g 44%) as grey crystals.

후처리

  1. additionThe reaction mixture is poured on ice-water/NH3conc
  2. extractionand extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto yield the crude product, which
  7. customis purified by recrystallisation from ethyl acetate/tert.butyl methyl ether

출처 및 근거

ORD 기록
ord-fe20243a49b742bf9cff00e9161f3605
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608072B1

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