Triisopropylsilyl chloride → 5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 574890Notes

Reaction equation

HRID 574890 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:21][CH:22]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH3:23]>O1CCCC1.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:23])[CH3:21])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 139400Triisopropylsilyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292235-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (15.4 g) in tetrahydrofuran (250 mL) was added 1M lithium hexamethyldisilazide in tetrahydrofuran (86 mL), and after 10 minutes, TIPS-Cl (triisopropylchlorosilane) (18.2 mL) was added. The mixture was stirred at room temperature for 24 hours. The reaction was diluted with ether, and the resulting solution was washed twice with water. The extracts were dried (Na2SO4), filtered, and concentrated. The crude product was chromatographed on silica gel with 10% ethyl acetate/hexanes.

Workup

  1. washthe resulting solution was washed twice with water
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3a47bb9a94e64fe59458895f48debe7e
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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