N,N'-Dimethylethylenediamine → 1-(6-Bromo-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine

HRID 57972

반응식

HRID 57972 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][NH:16][C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.[Br:17][C:18]1[C:23](OC)=[CH:22][CH:21]=[C:20](I)[N:19]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I>[Br:17][C:18]1[N:19]=[C:20]([N:16]2[C:10]3[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:13]=[CH:12][C:11]=3[CH:14]=[N:15]2)[CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 110990402-Bromo-6-iodo-3-methoxypyridineHCID 867070806-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 867071541-(6-Bromo-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine수율 64.6%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

반응 조건

온도
85 °C

실험 절차

A solution containing 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (250 mg, 1.18 mmol), 2-bromo-6-iodo-3-methoxypyridine (570 mg, 1.78 mmol), Copper(I) iodide (225 mg, 1.18 mmol), Potassium carbonate (196 mg, 1.42 mmol) and N,N′-Dimethylethylenediamine (0.25 mL, 2.37 mmol) was stirred at 85° C. 4 h. The reaction was filtered through celite and concentrated. The crude product purified by isco column (EtOAc/Hep eluted at 100% EtOAc) to give the desired product 280 mg 59% yield. MS (ESI) m/z: 397.1.

후처리

  1. custom4 h
  2. filtrationThe reaction was filtered through celite
  3. concentrationconcentrated
  4. customThe crude product purified by isco column (EtOAc/Hep eluted at 100% EtOAc)

출처 및 근거

ORD 기록
ord-bcdd45b0245d474dbf6f5047b3cb492c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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