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

HRID 1785589Notes

Reaction equation

HRID 1785589 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([Si](C(C)C)(C(C)C)C(C)C)[C:14]2=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 58835322Benzyl 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 57595581Benzyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 35.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a Round bottom flask was added compound 21 (250.0 mg, 0.0006118 mol) and Tetrahydrofuran (5.0 mL, 0.062 mol) and Tetra-n-butylammonium fluoride (190 mg, 0.00073 mol). The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with biotage to give product 22 (55 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with biotage

Sources & evidence

ORD record
ord-6103052002624290959dfc005b6a50fd
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

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