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

HRID 1261029Notes

Reaction equation

HRID 1261029 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 (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-bdb4da46877e492b82f7d595e9fef853
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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