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

HRID 1468978Notes

Reaction equation

HRID 1468978 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+].[CH:21]([Si:24]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])Cl)([CH3:23])[CH3:22]>O1CCCC1.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:24]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:21]([CH3:23])[CH3:22])[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, 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 residue was purified by flash chromatography, eluting with 10% ethyl acetate in hexanes to provide the title compound.

Workup

  1. washthe resulting solution was washed twice with water
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fe1b5e9ac7024fc8afef4b58d981ebe4
Source dataset
uspto-grants-2015_04
Patent number
US09006247B2

Reaction notes

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