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

HRID 1964874Notes

Reaction equation

HRID 1964874 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]pyridin (79, 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 (80, 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 (80, 0.40 g. 58% over 2 steps)

Sources & evidence

ORD record
ord-bfa34a2e980344aabb6c2650aa5c4ac5
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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