Formic Acid → 6-Chloro-3H-imidazo(4,5-c)pyridine

HRID 2409048

反応式

HRID 2409048 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[CH:10](O)=O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][CH:10]=[N:9][C:4]=2[CH:3]=1

参加物

3

反応物 2

HCID 284Formic AcidHCID 8171336-Chloropyridine-3,4-diamine

生成物 1

HCID 218138956-Chloro-3H-imidazo(4,5-c)pyridine収率 82%

実験手順

A mixture of 6-chloropyridine-3,4-diamine (4.00 g, 27.86 mmol) in formic acid (20.0 mL) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure to give a brown oil, which was partitioned between EtOAc (300 mL) and a sat'd aq NaHCO3 (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (6% to 9% MeOH) to afford 3.5 g (82%) of 6-chloro-3H-imidazo[4,5-c]pyridine as white solid, MS (ESI): m/z=154.1 [M+1]+.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto give a brown oil, which
  5. customwas partitioned between EtOAc (300 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by SiO2 chromatography
  10. washeluting with a MeOH/DCM gradient (6% to 9% MeOH)

出典と根拠

ORDレコード
ord-c8de8487b2a147cbb340f8525bd6e3f2
出典データセット
uspto-grants-2014_08
特許番号
US08815877B2

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