Potassium Carbonate → 2-(5-bromo-pyridin-3-yl)-5-methoxy-1-methyl-1H-benzoimidazole

HRID 1048988ノート

反応式

HRID 1048988 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:11])[C:6]([NH:9][CH3:10])=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=O)[CH:16]=[N:17][CH:18]=1.OOS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:12][C:13]1[CH:14]=[C:15]([C:19]2[N:9]([CH3:10])[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:11]=2)[CH:16]=[N:17][CH:18]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 45184444-methoxy-1-N-methylbenzene-1,2-diamineHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 666927982-(5-bromo-pyridin-3-yl)-5-methoxy-1-methyl-1H-benzoimidazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-methoxy-N1-methyl-benzene-1,2-diamine (34; 0.5 g, 0.00328 mol) and 5-bromo-pyridine-3-carbaldehyde (0.61 g, 0.00328 mol) in DMF (10 ml) and H2O (4 ml) was added OXONE® monopersulphate (2.42 g, 0.00394 mol). Reaction mass was stirred at room temperature for 3 h. The reaction mixture was basified with 10% K2CO3 solution to pH˜8-10 and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the crude compound which was purified by column chromatography to obtain title compound 2-(5-bromo-pyridin-3-yl)-5-methoxy-1-methyl-1H-benzoimidazole (35).

後処理

  1. customReaction mass
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto afford the crude compound which
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-9fc78bd795cc47be94b4ece473104db2
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

反応ノート

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