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Acetic Acid → 7-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine

HRID 500893
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HRID 500893 반응식
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[H-].[Na+].[C:13](O)(=O)C>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][N:8]([CH3:13])[C:7]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridine

생성물 1

HCID 594244767-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 259 (250mg, 1.64 mmol) in DMF (16 mL) at 0° C. was added NaH (197 mg, 4.92 mmol, 60% in mineral oil), and the mixture was stirred for 30 min, followed by addition of Mel (112 □L, 1.80 mmol). The reaction mixture was stirred at room temperature for 2 h before acetic acid (1 mL) was added. Solvents were removed under reduced pressure, the residue was partitioned between water and EtOAc. Organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1), to afford the title compound 263 (200 mg, 92% yield) as an off-white solid. MS (m/z): 167.1(M+H) (found).

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후처리

  1. additionfollowed by addition of Mel (112 □L, 1.80 mmol)
  2. additionwas added
  3. customSolvents were removed under reduced pressure
  4. customthe residue was partitioned between water and EtOAc
  5. customOrganic phase was collected
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1)

출처 및 근거

ORD 기록
ord-1aaada9a5f964226bd5f1ccd4d700ad5
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772247B2

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