Iodine → 4-Bromo-2-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.C([N-]C(C)C)(C)C.[Li+].CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C.[I:49]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]([I:49])=[CH:10][C:3]=12Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
To a solution of Example 36A (25 g, 71.2 mmol) in tetrahydrofuran (600 mL) at −78° C. was added slowly 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethyl benzene (39.1 mL, 78 mmol) and the mixture was stirred at −78° C. for 1 hour. A solution of iodine (19.87 g, 78 mmol) in tetrahydrofuran (100 mL) was added slowly and the reaction was allowed to warm gradually to room temperature. The reaction mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium thiosulfate and water were added and the mixture was extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated to give the title compound.
Workup
- temperatureto warm gradually to room temperature
- stirringThe reaction mixture was stirred at room temperature for 3 hours
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe combined organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5499a85e81b44196befc737e034ff084
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969375B2
Reaction notes
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