N-Iodosuccinimide → 3-Iodo-5-methyl-1-(triisopropylsilyl)-1h-pyrrolo[2,3-b]pyridine
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1.[I:21]N1C(=O)CCC1=O>ClCCl>[I:21][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:18]([CH3:20])[CH3:19])[CH:9]=1Participants
4
Procedure
5-Methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (8, 1.1 g, 3.8 mmol) and 10 mL of dichloromethane were combined in a round bottom flask and stirred for 10 minutes. A slurry of N-iodosuccinimide (1.0 g, 4.6 mmol) in 5 mL of dichloromethane was added and stirred at room temperature overnight. The reaction was quenched with sodium thiosulfate (20 mL, 1M in water) and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexanes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a light yellow oil (9, 1.2 g, 75%). MS (ESI) [M+H+]+=415.08.