Water → 4-Bromo-6-chloro-1-methyl-1H-benzo[d]imidazole

HRID 1024042노트

반응식

HRID 1024042 반응식
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:12])[C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866841377-Bromo-5-chloro-1H-benzimidazole

생성물 1

HCID 866841384-Bromo-6-chloro-1-methyl-1H-benzo[d]imidazole수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 109c (3.5 g, 15 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.14 g, 30 mmol) and iodomethane (1.4 mL, 22.7 mmol). The reaction was stirred at room temperature for overnight. Water (50 mL) was added to quench the reaction and the resulting mixture was extracted with ethyl acetate (5 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (from 4:1 to 1:2) to afford 109d as a white solid (1.4 g, 38%). LCMS: [M+H]+ 245/247. 1H NMR (500 MHz, CDCl3) δ 7.89 (s, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H), 3.81 (s, 3H).

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe resulting mixture was extracted with ethyl acetate (5 mL×3)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with petroleum ether/ethyl acetate (from 4:1 to 1:2)

출처 및 근거

ORD 기록
ord-553315657c694829a329b6c4009c7049
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722676B2

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