Methyl iodide → 4-(6-Fluoropyridin-3-yl)-1-methylpyrrolidin-2-one

HRID 595923노트

반응식

HRID 595923 반응식
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:17]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH3:17])[C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodide2회HCID 24758Sodium hydride2회HCID 1180464264-(6-Fluoropyridin-3-yl)pyrrolidin-2-one

생성물 1

HCID 1180458344-(6-Fluoropyridin-3-yl)-1-methylpyrrolidin-2-one수율 58%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To 4-(6-fluoropyridin-3-yl)pyrrolidin-2-one (200 mg, 0.888 mmol) in DMF (4 mL) in ice bath was added NaH (42.6 mg, 1.066 mmol) and iodomethane (0.067 mL, 1.066 mmol). The reaction mixture was stirred in ice bath for 30 min and room temperature for 1 hour. LC-MS shows mixture of SM and product (1:1). Added again NaH (42.6 mg, 1.066 mmol) and iodomethane (0.067 mL, 1.066 mmol), stirred for 1 h at room temperature. Complete reaction by LC-MS. Reaction mixture was diluted with EtOAc and washed with water and bine. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography [0-50-80% EtOAc (contains 10% MeOH)/heptane]. LCMS (m/z): 195.2 (MH+), 0.492 min. Yield 58%

후처리

  1. waitroom temperature for 1 hour
  2. additionmixture of SM and product (1:1)
  3. stirringstirred for 1 h at room temperature
  4. customreaction by LC-MS
  5. customReaction mixture
  6. washwashed with water and bine
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude was purified by flash chromatography [0-50-80% EtOAc (contains 10% MeOH)/heptane]
  11. custom195.2 (MH+), 0.492 min

출처 및 근거

ORD 기록
ord-3e7af4c68f7e448aacdd99f4c591b64f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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