Tetrahydrofuran → 5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515901Notes

Reaction equation

HRID 1515901 reaction equation
C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([S:15][CH2:16][CH3:17])[CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH2:16]([S:15][C:13]1[CH:14]=[C:9]2[CH:8]=[CH:7][NH:6][C:10]2=[N:11][CH:12]=1)[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 672294871-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672279375-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridineYield 48%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.5 g, 8.68 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1 M, 9.11 mL, 9.11 mmol) was stirred for 2 h at room temperature. The mixture was poured into brine (15 mL), extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes) afforded 5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (600 mg, 48%) as a white solid which was used in the next step without purification: LC/MS m/e calcd for C9H10N2O [M+H]+ 179.26, observed 179.2.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with a saturated aqueous ammonium chloride solution (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7cb8f774f3d440a6b46ec4e0596852f8
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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