Tetrabutylammonium Fluoride → H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-(3-furanyl)-

HRID 2114039Notes

Reaction equation

HRID 2114039 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:15]=[CH:14][O:13][CH:12]=3)=[C:9]([Si](C)(C)C)[NH:8][C:5]2=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:15]=[CH:14][O:13][CH:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 598118725-Bromo-3-furan-3-yl-2-trimethylsilanyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59811896H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-(3-furanyl)-Yield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of azaindole 13 (20.9 mg, 0.06 mmol) in THF (3 mL) was added a 1M solution of TBAF in THF (0.12 mL, 0.12 mmol). After 1.5 h the mixture was concentrated and purified by PTLC with AcOEt as eluent to give azaindole 14 (9.6 mg, 58%) as a white solid. 1H NMR (400 MHz; CDCl3) δ 6.67 (m, 1H), 7.44 (d, J=2.4 Hz, 1H), 7.53 (m, 1H), 7.76 (m, 1H), 8.18 (d, J=2.1 Hz, 1H), 8.39 (m, 1H), 9.33 (brs, NH).

Workup

  1. concentrationAfter 1.5 h the mixture was concentrated
  2. custompurified by PTLC with AcOEt as eluent

Sources & evidence

ORD record
ord-8a19bc40a0db48b69c68728fb19c1ad6
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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