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 the solution of triphenylphosphine (2.56 g; 9.65 mmol) in THF (30 mL). The mixture was stirred at room temperature for 30 min. To this green suspension was added a solution of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2.00 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 crude material was purified by flash chromatography (eluent: 5 to 40% of ethyl acetate in heptanes) 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 crude material was purified by flash chromatography (eluent: 5 to 40% of ethyl acetate in heptanes)
Sources & evidence
- ORD record
- ord-1504e64caf53435b9df18058f9d387df
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434722B2
Linked notes
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