Methyl iodide → N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]-N-methylbenzamide

HRID 25780노트

반응식

HRID 25780 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH3:22])([CH3:21])[CH:15]=[C:14]2[CH2:23][NH:24][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:33]I>C1COCC1>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH3:22])([CH3:21])[CH:15]=[C:14]2[CH2:23][N:24]([CH3:33])[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2회HCID 10408574N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide

생성물 1

HCID 10047312N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]-N-methylbenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A round bottom flask equipped with a stir bar and under argon atmosphere was charged with NaH (60% in oil) (0.04 mmol, 1 equiv) and 1 mL of THF. Another vessel containing N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide (Example 3) was diluted with THF and this solution was added to the NaH solution. Lastly, MeI (0.06 mmol, 1.5 equiv) was added and the reaction was stirred 5 hours under argon. The reaction was quenched with water and extracted with EtOAc. The combined organics were subsequently washed with brine and concentrated in vacuo. The residue was taken up in methylene chloride and adsorbed onto silica gel and flash chromatographed using 25% EtOAc/hexanes to elute product. The product fractions were pooled and concentrated in vacuo to afford 7.2 mg of the title compound as a oil.

후처리

  1. customA round bottom flask equipped with a stir bar and under argon atmosphere
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organics were subsequently washed with brine
  5. concentrationconcentrated in vacuo
  6. customchromatographed
  7. washto elute product
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0eb4617eb36e4b14a892de333652ca24
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858627B2

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