Sodium cyanoborohydride → HCID 21717362, compound

HRID 1386071Notes

Reaction equation

HRID 1386071 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH:18]=O)[CH3:15].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][NH:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH3:15]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 22672632HCID 22672632, compoundHCID 229974692-Ethyl-6-methylbenzaldehyde

Product 1

HCID 21717362HCID 21717362, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 8-amino-2,3,6-trimethylimidazo[1,2-a]pyridine (0.5 g, 2.8 mmol), 2-ethyl-6-methylbenzaldehyde (0.45 g, 3 mmol) and zinc(II)chloride (0.4 g, 3 mmol) in 50 ml methanol was treated with sodium cyanoborohydride (0.19 g, 3 mmol) and refluxed for 20 h. The methanol was evaporated under reduced pressure and the residue was dissolved in dichloromethylene and water. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on silicagel with dichloromethylene:methanol (10:1) which yielded 0.28 g (33%) of the title compound.

Workup

  1. temperaturerefluxed for 20 h
  2. customThe methanol was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethylene
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silicagel with dichloromethylene:methanol (10:1) which

Sources & evidence

ORD record
ord-d0cff468a59141b48036f99aff1afe30
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

Loading…