Tetrabutylammonium Fluoride → 2-(1H-pyrrol-3-yl)Pyridine

HRID 2222269Notes

Reaction equation

HRID 2222269 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6]1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69314044HCID 69314044, compound

Product 1

HCID 8203972-(1H-pyrrol-3-yl)Pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]pyridine (1 g, 3.2 mmol) in anhydrous THF (15 mL) was added TBAF (3.84 mL of a 1M solution in THF, 3.84 mmol). After stirring for 10 min. at rt, the reaction was complete. The reaction mixture quenched with H2O (40 mL), extracted with EtOAc (3×25 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and chromatographed on silica gel eluting with EtOAc:hexane (1:1) to afford 2-(1H-pyrrol-3-yl)pyridine as a solid. 1H NMR (CD3Cl, 300 MHz) δ 8.55 (ddd, 1H), 7.65 (dt, 1H), 7.54 (dd, 1H), 7.46˜7.43 (d, 1H), 7.07 (ddd, 1H), 6.85 (dd, 1H), 6.74 (dd, 1H). MS (ESI) 145.1 (M++H).

Workup

  1. customThe reaction mixture quenched with H2O (40 mL)
  2. extractionextracted with EtOAc (3×25 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel eluting with EtOAc:hexane (1:1)

Sources & evidence

ORD record
ord-12de3f8b98354abfa8e6e8d6c7593b3c
Source dataset
uspto-grants-2008_05
Patent number
US07371767B2

Reaction notes

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