N-Iodosuccinimide → 6-Chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

HRID 2203342노트

반응식

HRID 2203342 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[N:9][CH:10]=2)[CH:7]=1.C1C(=O)N([I:27])C(=O)C1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[N:9][C:10]=2[I:27])[CH:7]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 866789776-Chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

생성물 1

HCID 866789786-Chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the intermediate from Step G (3.64 g, 12.19 mmol) in anhydrous DCM (50 mL) was added NIS (5.48 g, 24.4 mmol). The reaction mixture was stirred at room temperature for 18 hours and concentrated. The residue was suspended in ethyl acetate and washed with saturated sodium thiosulfate (2×). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give a bright white solid. m/z=424.7 (M+H).

후처리

  1. concentrationconcentrated
  2. washwashed with saturated sodium thiosulfate (2×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. customto give a bright white solid

출처 및 근거

ORD 기록
ord-5094bc3808084fb6a8c49fd0f2f919aa
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365574B2

반응 노트

불러오는 중…