Tetrabutylammonium Fluoride → 5-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 253365Notes

Reaction equation

HRID 253365 reaction equation
[Cl:1][C:2]1[CH:3]=[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.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 242292415-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (3, 1.40 g, 4.53 mmol) in tetrahydrofuran (15 mL) was added tetra-n-butylammonium fluoride (1.42 g, 5.43 mmol). The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated and isolated by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the compound (4, 0.40 g. 58% over 2 steps). MS (ESI) [M−H+]−=153.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customisolated by silica gel column chromatography
  3. washeluting with 30% ethyl acetate in hexane
  4. customto give the compound (4, 0.40 g. 58% over 2 steps)

Sources & evidence

ORD record
ord-84cb1acf2e544bddafa0ac1131f57537
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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