Sodium Pyrosulfite → 1-(4-Cyanophenyl)-2-trifluoromethylimidazo[4,5-c]pyridine

HRID 892762노트

반응식

HRID 892762 반응식
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.O.[F:18][C:19]([F:23])([F:22])[CH:20]=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C)C(=O)C.C(OCC)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=[C:20]2[C:19]([F:23])([F:22])[F:18])=[CH:10][CH:11]=1)#[N:16]

참가 물질

6

반응물 3

HCID 656671Sodium PyrosulfiteHCID 27813662,2,2-Trifluoroacetaldehyde hydrateHCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridine

생성물 1

HCID 150053981-(4-Cyanophenyl)-2-trifluoromethylimidazo[4,5-c]pyridine

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (420 mg, 2.0 mmol) (prepared as above), trifluoroacetaldehyde hydrate (232 mg, 2.0 mmol), and sodium metabisulphite (475 mg, 2.5 mmol) in N,N-dimethylacetamide (10 ml) was heated under reflux for 16 hours. After being cooled, the mixture was diluted with ethyl acetate (200 ml), washed with saturated aqueous sodium bicarbonate (50 ml) and water (5×50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with ethyl acetate) to give 1-(4-cyanophenyl)-2-trifluoromethylimidazo[4,5-c]pyridine, 337 mg.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter being cooled
  4. washwashed with saturated aqueous sodium bicarbonate (50 ml) and water (5×50 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (eluting with ethyl acetate)

출처 및 근거

ORD 기록
ord-308a41b3b3004af7b125d2b5a33893be
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05120747

반응 노트

불러오는 중…