Phosphorus tribromide → 1-benzenesulfonyl-2-bromomethyl-5-chloro-1H-pyrrolo[3,2-b]pyridine
Reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[N:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:20]O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:23]>CCOCC.C(Cl)Cl.O.CCOC(C)=O>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[N:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:20][Br:23])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (1-benzenesulfonyl-5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)-methanol (0.16 g, 0.50 mmol) in 4 mL Et2O/CH2Cl2 (1:1) at 0° C. is added phosphorous tribromide (0.023 mL, 0.25 mmol) dropwise. The reaction vessel is kept in the dark and stirred at 0° C. for 1 hour, then at room temperature for 2 hours. The mixture is diluted with water and EtOAc and the layers are separated. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with water, saturated NaHCO3 solution and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude product (0.16 g, 0.41 mmol) is used in the subsequent step without further purification.
Workup
- waitat room temperature for 2 hours
- customthe layers are separated
- extractionThe aqueous layer is extracted with EtOAc
- washThe combined organic layers are washed with water, saturated NaHCO3 solution and saturated NaCl solution
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c64473eb2c1f46a78d680ef6b9c0e3b0
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06281227B1
Reaction notes
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