Hexachloroethane → 5-Chloro-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

HRID 408156Notes

Reaction equation

HRID 408156 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.[Li]C(CC)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:26][C:7]1[C:2]([F:1])=[C:3]2[CH:10]=[CH:9][N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[C:4]2=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 112663344-Fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 178418400CID 53628100

Product 1

HCID 602052735-Chloro-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 10.258 mmol) was placed in THF (15 mL) at −78° C. s-BuLi (16.12 mL, 22.57 mmol) was then added dropwise and stirred for 30 minutes. Hexachloroethane (6.07 g, 25.6 mmol) in THF (10 mL) was then added rapidly, and the reaction was stirred for an additional 30 minutes. The reaction was quenched with saturated aqueous NH4Cl and extracted into hexanes. The combined organic fractions were dried, filtered and concentrated to give the crude product that was purified by column chromatography (hexanes) to give 5-chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (2.1 g, 62% yield).

Workup

  1. additionwas then added dropwise
  2. stirringthe reaction was stirred for an additional 30 minutes
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. extractionextracted into hexanes
  5. customThe combined organic fractions were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product that
  9. customwas purified by column chromatography (hexanes)

Sources & evidence

ORD record
ord-49cb7db41dfd4434b69dbc24930550ed
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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