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 419155Notes

Reaction equation

HRID 419155 reaction equation
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]

Participants

5

Reactant 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, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4ba99436508f4e069f2a8d1296356bf1
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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