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

HRID 1890618ノート

反応式

HRID 1890618 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-9f1e17db921a4067b3966f3a87bf8b15
出典データセット
uspto-grants-2013_08
特許番号
US08507484B2

反応ノート

読み込み中…