Benzenesulfonyl chloride → 4-Iodo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine
Reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][N:11]=[CH:12][C:5]=12.C(N(CC)CC)C.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.CN(C=O)C>[I:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]([S:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:28])=[O:27])[N:11]=[CH:12][C:5]=12Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirring suspension of NaH (0.9 g) in anhydrous THF (25 ml) at −5° C. was added 4-iodo-1H-pyrazolo[3,4-b]pyridine (5 g) in anhydrous THF (75 ml) and DMF (25 ml). Triethylamine (3 ml) was added and the reaction was stirred for 30 min at 0° C. Benzenesulfonyl chloride (2.9 ml) in anhydrous THF (25 ml) was added dropwise over 10 min and the reaction was stirred for 1 h at 0° C. then quenched with water. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered and then evaporated to yield a solid residue that was triturated with methanol to give title compound, 4.1 g.
Workup
- stirringthe reaction was stirred for 1 h at 0° C.
- customthen quenched with water
- customThe layers were separated
- extractionthe aqueous was re-extracted with ethyl acetate
- washThe combined organics were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customto yield a solid residue that
- customwas triturated with methanol
Sources & evidence
- ORD record
- ord-ed99858463594ecb8954c910cbc048c7
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658635B2
Reaction notes
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