2-Pyridinamine, N-methyl- → 1-Ethyl-N-methyl-N-pyridin-2-yl-1H-benzimidazol-2-amine

HRID 495265

反応式

HRID 495265 の反応式
Br[C:2]1[N:6]([CH2:7][CH3:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N:3]=1.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N:3]=[C:2]1[N:14]([CH3:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:8]

参加物

5

反応物 3

HCID 207272-Pyridinamine, N-methyl-HCID 23676156Sodium t-butoxideHCID 666281632-Bromo-1-ethyl-1H-benzo[d]imidazole

生成物 1

HCID 666282671-Ethyl-N-methyl-N-pyridin-2-yl-1H-benzimidazol-2-amine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a flask were added 11.0 g of 2-bromo-1-ethyl-1H-benzimidazole, 0.48 2-(methylamino)pyridine, 0.64 g of sodium tert-butoxide, and 25 ml toluene. The mixture was purged thoroughly with nitrogen and 250 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene and 64 mg of palladium acetate were added. The reaction mixture was heated to 90 C for 16 hours, and then cooled to 22 C. After quenching with 50 ml water, the product was extracted with 20 ml ethyl acetate. The product was extracted with 30 ml of 1M hydrochloric acid, and then basified with 3M sodium hydroxide. Following extraction with 20 ml ethyl acetate, the product was purified by silica gel chromatography using a gradient from 40% ethyl acetate in hexane to 70% ethyl acetate in hexane, resulting in 0.6 g of a yellow oil which crystallized on standing. The product was recrystallized from a mixture of 5 ml hexane with 1.5 ml 2-propanol. After filtration and drying of the product, a 0.44 g of a yellow solid was obtained.

後処理

  1. customThe mixture was purged thoroughly with nitrogen and 250 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene and 64 mg of palladium acetate
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 90 C for 16 hours
  4. temperaturecooled to 22 C
  5. customAfter quenching with 50 ml water
  6. extractionthe product was extracted with 20 ml ethyl acetate
  7. extractionThe product was extracted with 30 ml of 1M hydrochloric acid
  8. extractionextraction with 20 ml ethyl acetate
  9. customthe product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-453eb4cb87b3433f8f901d3d210a6246
出典データセット
uspto-grants-2009_05
特許番号
US07538931B2

関連ノート

読み込み中…