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

HRID 1515919Notes

Reaction equation

HRID 1515919 reaction equation
C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH3:15][C:13]1[CH:14]=[C:9]2[CH:8]=[CH:7][NH:6][C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 575978501-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 205974295-methyl-1H-pyrrolo[2,3-b]pyridineYield 82.2%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(tert-butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine (7.92 g, 32.2 mmol) and a solution tetrabutylammonium fluoride in tetrahydrofuran (1 M, 161 mL, 161 mmol) was stirred for 2 h at room temperature. The mixture was poured into brine (50 mL), extracted with ethyl acetate (2×200 mL), washed with a saturated aqueous ammonium chloride solution (3×60 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by a flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes) afforded 5-methyl-1H-pyrrolo[2,3-b]pyridine (3.5 g, 82%) as a white solid: LC/MS m/e calcd for C8H8N2 [M+H]+ 133.17, observed 133.0.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washwashed with a saturated aqueous ammonium chloride solution (3×60 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by a flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a46dbfc6586346b48463c47dd620abdf
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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