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

HRID 2107668ノート

反応式

HRID 2107668 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6dadc40019d34a0697f4c336849e3579
出典データセット
uspto-grants-1990_06
特許番号
US04935430

反応ノート

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