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

HRID 1034669Notes

Reaction equation

HRID 1034669 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+:11]([CH2:20]CCC)(CCCC)CCCC.[F-:24].[CH2:25]([Cl:27])Cl>C1COCC1>[Cl:27][C:25]1[C:4]([F:24])=[C:5]2[CH:3]=[CH:2][NH:1][C:6]2=[N:11][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 534129535-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2, 3-1)]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-d9f4b45e01124433904a9fb6dec9134c
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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