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

HRID 1515600Notes

Reaction equation

HRID 1515600 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][N:26]([Si](C(C)(C)C)(C)C)[C:23]2=[N:24][CH:25]=1>O1CCCC1>[Br:19][C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 497590181H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-

Product 1

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Tetrabutylammonium fluoride (1 M solution in tetrahydrofuran) (58.5 mL, 58.5 mmol) was added to a solution of 5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine (16.5 g, 53 mmol) in tetrahydrofuran (15 mL) at 25° C. The mixture was stirred at 25° C. for 30 min and then extracted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to afford 5-bromo-1H-pyrrolo[2,3-b]pyridine (7.4 g, 71%) as a light yellow solid: LC/MS m/e calcd for C7H6BrN [M+H]+ 198.04, observed 197.1, 199.1; 1H NMR (400 MHz, CDCl3) δ ppm 6.49 (m, 1H), 7.39 (m, 1H), 8.10 (s, 1H), 8.38 (s, 1H), 10.48 (br. s., 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8c812d4db14646d5908367472c77f6b1
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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