Dichloromethane → 5-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine

HRID 408173Notes

Reaction equation

HRID 408173 reaction equation
[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(Cl)Cl>C1COCC1>[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 602052735-Chloro-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534129535-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridineYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 9.2 mmol) in THF (15 mL) at 0° C. was treated dropwise with TBAF (10.1 mL, 10.1 mmol). After 30 minutes, the reaction was quenched with saturated aqueous NaHCO3 and extracted into CH2Cl2. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude was purified by flash chromatography on silica gel using 1.2% MeOH:CH2Cl2 to provide 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.4 g, 89% yield).

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted into CH2Cl2
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography on silica gel using 1.2% MeOH

Sources & evidence

ORD record
ord-caf901fffa5c41b7bf32157188433bdc
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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