Imidazole → 5-Triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridine

HRID 1754684Notes

Reaction equation

HRID 1754684 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([OH:10])[CH:9]=[C:4]2[CH:3]=[CH:2]1.N1C=CN=C1.[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17].ClCCl>CN(C)C=O>[CH:16]([Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[O:10][C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 139400Triisopropylsilyl chlorideHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-ol

Product 1

HCID 595933245-Triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridineYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-Pyrrolo[2,3-b]pyridin-5-ol (0.5 g, 0.004 mol) and 1H-imidazole (0.98 g, 0.014 mol) in N,N-dimethylformamide (5 mL) was added triisopropylsilyl chloride (1 mL, 0.005 mol). The reaction mixture was stirred at room temperature overnight. Dichloromethane (10 mL) was added and the solution was washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a viscous liquid (83, 0.4 g, 40%).

Workup

  1. washthe solution was washed with brine
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of solvent
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-3fd3ab8d4acd44ef83ebadf1d3c8fa23
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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