Ethyl Acetate → Ethyl [3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]acetate

HRID 390546노트

반응식

HRID 390546 반응식
C(OCC[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH3:16])=[N:8]1)(=O)C.C1C(=O)N([Br:24])C(=O)C1.[CH3:25][CH2:26][O:27][C:28]([CH3:30])=[O:29]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:26]([O:27][C:28](=[O:29])[CH2:30][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH2:16][Br:24])=[N:8]1)[CH3:25]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 67103879HCID 67103879, 화합물

생성물 1

HCID 57642772Ethyl [3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]acetate

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of (3-methyl-pyrazolo[3,4-b]pyridine-1-yl)ethyl acetate (2.5 mmol, 1 eq.), NBS (3.0 mmol, 1.2 eq.), and benzoyl peroxide (0.05 mmol, 0.02 eq.) in 10 mL of CCl4 was refluxed for 1.5 h. The resultant mixture was cooled to rt, and diluted with 500 mL of EtOAc. The resultant solution was then washed with 100 mL of sat. sodium bicarbonate aqueous solution, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (20% EtOAc in hexane to 35% EtOAc in hexane) to provide 450.2 mg of the desired product: HPLC retention time=2.50 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 0% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expect=298.0. found=298.3.

후처리

  1. temperaturewas refluxed for 1.5 h
  2. washThe resultant solution was then washed with 100 mL of sat. sodium bicarbonate aqueous solution, brine solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by silica gel chromatography (20% EtOAc in hexane to 35% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-e63616dabe2548b7a083ef02ce44932d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383630B2

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