Ammonium formate → 4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamine

HRID 1890618Notes

Reaction equation

HRID 1890618 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:13]2[C:6]3=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]3[N:4]=[C:3]2[CH2:1][CH3:2])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 104031282-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 100165294-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamineYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine (4.81 g, 15.5 mmol) obtained in Step 1 was dissolved in methanol (155 mL) and palladium/carbon (10%, wet, 1.65 g, 1.55 mmol) and ammonium formate (9.77 g, 155 mmol) were added to the solution, followed by stirring at room temperature for 40 minutes. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue and precipitated crystals were collected by filtration and washed with water. Ethyl acetate-hexane (2:3) was added to the obtained crude crystals and the mixture was stirred under reflux for 1 hour. After cooling to room temperature, the precipitated crystals were collected by filtration to obtain Compound P7 (3.53 g, 12.6 mmol, yield 81.2%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. customprecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. additionEthyl acetate-hexane (2:3) was added to the
  8. customobtained crude crystals
  9. stirringthe mixture was stirred
  10. temperatureunder reflux for 1 hour
  11. temperatureAfter cooling to room temperature
  12. filtrationthe precipitated crystals were collected by filtration
  13. customto obtain Compound P7 (3.53 g, 12.6 mmol, yield 81.2%)

Sources & evidence

ORD record
ord-9f1e17db921a4067b3966f3a87bf8b15
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

Loading…