Carbon tetrabromide → 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:25][C:26]1[CH:27]=[C:28]2[C:34]([CH2:35]CO)=[C:33]([Si:38]([CH2:43][CH3:44])([CH2:41][CH3:42])[CH2:39][CH3:40])[NH:32][C:29]2=[N:30][CH:31]=1>C1COCC1>[Br:5][CH2:1][CH2:35][C:34]1[C:28]2[C:29](=[N:30][CH:31]=[C:26]([Cl:25])[CH:27]=2)[NH:32][C:33]=1[Si:38]([CH2:39][CH3:40])([CH2:43][CH3:44])[CH2:41][CH3:42]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Carbon tetrabromide (3.27 g, 9.65 mmol) was added to a solution of triphenylphosphine (2.56 g; 9.65 mmol) in THF (30 mL). The mixture was stirred at room temperature for 30 minutes. To this green suspension was added a solution of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2 g; 6.43 mmol) in THF (20 mL) and the resulting reaction mixture was stirred for 20 hours. The precipitate was eliminated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (eluent 5 to 40% ethyl acetate in heptane) to give 1.08 g (45%) of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid.
Workup
- customthe resulting reaction mixture
- stirringwas stirred for 20 hours
- filtrationThe precipitate was eliminated by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by flash chromatography (eluent 5 to 40% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-d610fbfc39a14794985643cf250607fa
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266832B2
Reaction notes
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