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

HRID 875660Notes

Reaction equation

HRID 875660 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-43db0a93841c43a986f7fc6a55a7242a
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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