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

HRID 1048988

반응식

HRID 1048988 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9fc78bd795cc47be94b4ece473104db2
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382226B2

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