Iodine → 5-(3,4-Dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[I:20]I.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[C:19]([I:20])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Participants
Conditions
- Temperature
- -40 °C
Procedure
5-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine, 82, (0.270 g, 0.00106 mol) was dissolved in Tetrahydrofuran (8.5 mL, 0.10 mol) under an atmosphere of Nitrogen. The solution was stirred at −40° C. and Iodine (0.269 g, 0.00106 mol) dissolved in 2.5 mL of Tetrahydrofuran was added. The chilled reaction mixture was stirred for 2 h and was then quenched with the addition of Sodium thiosulfate, pentahydrate (0.13 g, 0.00053 mol) in water (1M). The reaction mixture was partitioned between water (20 mL and ethyl acetate (30 mL). The two layers were seperated, and the aquous layer was extracted with ethyl acetate. The organic layers were washed with water and brine, dried with sodium sulfate, then concentrated under reduced pressure. The dark colored crude residue was carried onto the next reaction without further purification.
Workup
- additionwas added
- customThe chilled reaction mixture
- stirringwas stirred for 2 h
- customThe reaction mixture was partitioned between water (20 mL and ethyl acetate (30 mL)
- customThe two layers were seperated
- extractionthe aquous layer was extracted with ethyl acetate
- washThe organic layers were washed with water and brine
- dry with materialdried with sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe dark colored crude residue was carried onto the next reaction without further purification
Sources & evidence
- ORD record
- ord-7b79f6b007bb4427876698b4723b5ba2
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605168B2
Reaction notes
Loading…