Ethylene Glycol → 5-bromo-1-methyl-3-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 879497노트

반응식

HRID 879497 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([N:17]3[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]3)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 531671-MethylpiperazineHCID 62657Potassium Phosphate, TribasicHCID 598120775-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 867003145-bromo-1-methyl-3-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매

실험 절차

A solution of 5-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.445 mmol), 1-methylpiperazine (356.7 mg, 3.56 mmol), copper(I) iodide (84.8 mg, 0.445 mmol), K3PO4 (378 mg, 1.78 mmol), 1,2-ethanediol (138 mg, 2.225 mmol) in isopropyl alcohol (5 mL) in a sealed tubes was heated at 70° C. for 2 days. After cooling to room temperature, the reaction mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was taken up in EtOAc and the solution was washed with saturated NaHCO3, dried and concentrated. Purification by flash chromatography afforded the title compound. LCMS-ESI+: calc'd for C13H17BrN4 309.1 (M+H+); Found: 309.1 (M+H+).

후처리

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. washthe solution was washed with saturated NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-6441f764584b43f98fe5d25f8949256d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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