Water → 5-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

HRID 79523Notes

Reaction equation

HRID 79523 reaction equation
[Br:1][C:2]1[C:3]([Cl: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-].O>C1COCC1>[Br:1][C:2]1[C:3]([Cl:21])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 575376865-Bromo-4-chloro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 457897885-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridineYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (4.1 g, 10.57 mmol, see Example 1) was placed in THF (80 mL) at room temperature. TBAF (1.1 equivalents) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was then poured into water and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude solid. The solid was then suspended in 10:1 hexanes:DCM, and filtered to give the solid product 5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (2.20 g, 89.9% yield).

Workup

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid
  6. filtrationDCM, and filtered

Sources & evidence

ORD record
ord-d51195f055ed4ef796c14cede692b76e
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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