Water → 5-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

HRID 253364Notes

Reaction equation

HRID 253364 reaction equation
Br[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.C([Li])(C)(C)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl.O>O1CCCC1>[Cl:26][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

Participants

6

Reactant 4

HCID 962WaterHCID 6214HexachloroethaneHCID 242292235-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 242292415-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridineYield 114.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-bromo-1-triisopropylsilyl-7-azaindole (2, 1.60 g, 4.53 mmol) in tetrahydrofuran (50.0 mL), under an atmosphere of nitrogen at −78° C., was added tert-butyllithium (1.70 M in hexane, 6.12 mL). The reaction was stirred for 1 hour, followed by addition of hexachloroethane (1.29 g, 5.43 mmol). The reaction was stirred for 3 hours, poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give the crude compound (3, 1.60 g). MS (ESI) [M+H+]+=309.3.

Workup

  1. stirringThe reaction was stirred for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f40d893989294767b93e9b84a0cbb4ca
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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