4-Iodo-1H-pyrazolo[3,4-b]pyridine → 4-Chloro-N-[5-chloro-2-(1H-pyrazolo[3,4-b]pyridine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 419155노트

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HRID 419155 반응식
I[C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C([Mg]Cl)(C)C.CON(C)[C:19]([C:21]1[C:26]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=2)(=[O:30])=[O:29])=[CH:25][C:24]([Cl:42])=[CH:23][N:22]=1)=[O:20]>C1COCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([NH:27][C:26]2[C:21]([C:19]([C:2]3[C:3]4[CH:4]=[N:5][NH:6][C:7]=4[N:8]=[CH:9][CH:10]=3)=[O:20])=[N:22][CH:23]=[C:24]([Cl:42])[CH:25]=2)(=[O:30])=[O:29])=[CH:32][C:33]=1[C:38]([F:39])([F:41])[F:40]

참가 물질

5

반응물 3

HCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridineHCID 579421055-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 441775994-Chloro-N-[5-chloro-2-(1H-pyrazolo[3,4-b]pyridine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 4-iodo-7-azaindazole (Potashman et. al., WO2005070891) (123 mg) in THF (2 mL) at 0° C. was added isopropylmagnesium chloride (2 M solution in THF, 0.5 mL). The mixture was stirred at 0° C. for 30 min and 5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid methoxy-methyl-amide (114 mg) was added. The reaction mixture was warmed to room temperature, stirred for 2 h and quench by saturated aqueous NH4Cl solution (2 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (5 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by flash chromatography (silica) to afford the title compound as a white powder. MS (M+H)+: 515.9.

후처리

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 2 h
  3. customquench by saturated aqueous NH4Cl solution (2 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (5 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography (silica)

출처 및 근거

ORD 기록
ord-4ba99436508f4e069f2a8d1296356bf1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093247B2

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