Benzenesulfonyl chloride → 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine
Reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]2[NH:10][CH:11]=[CH:12][C:5]=12.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[Br:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]2[N:10]([S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:11]=[CH:12][C:5]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
To a stirring suspension of NaH (1.3 g) in anhydrous THF (25 ml) at −5° C. was added 4-bromo-1H-pyrrolo[2,3-c]pyridine (prepared for example as described in patent US2005/0090529, 5 g) in anhydrous THF (75 ml) over 10 min. The reaction was stirred at −5° C. for 10 min then benzenesulfonyl chloride (3.6 ml) in anhydrous THF (25 ml) was added over 10 min. The reaction was stirred at 0° C. for 1 h then quenched with water. The layers were separated and the aqueous was re-extracted with ethyl acetate. The organics were combined, washed with brine, dried over magnesium sulfate, filtered and then evaporated to yield a residue that was triturated using methanol (25 ml). The resulting solid was collected by filtration, washed sparingly with methanol then dried in vacuo at 45° C. overnight to give title compound, 7.9 g.
Workup
- stirringThe reaction was stirred at 0° C. for 1 h
- customthen quenched with water
- customThe layers were separated
- extractionthe aqueous was re-extracted with ethyl acetate
- washwashed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customto yield a residue that
- customwas triturated
- filtrationThe resulting solid was collected by filtration
- washwashed sparingly with methanol
- customthen dried in vacuo at 45° C. overnight
Sources & evidence
- ORD record
- ord-233cae2f4a3e47718db966d8b8fba2e2
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658635B2
Reaction notes
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