TBAF tetrahydrofuran → HCID 23156128, compound

HRID 1890635Notes

Reaction equation

HRID 1890635 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([CH:35]=[CH:36][CH:37]=2)[C:18]([C:20]2[CH:34]=[CH:33][C:23]([CH2:24][O:25][Si](C(C)(C)C)(C)C)=[CH:22][CH:21]=2)=[O:19])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1.C(OCC)(=O)C>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([CH:35]=[CH:36][CH:37]=2)[C:18]([C:20]2[CH:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:33][CH:34]=2)=[O:19])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69435422HCID 69435422, compound

Product 1

HCID 23156128HCID 23156128, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

{4-[3-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)benzoyl]benzyloxy)-tert-butyldimethylsilane (0.898 g, 1.75 mmol) obtained in Step 4 was dissolved in THF (15 mL), and a 1.0 mol/L TBAF-THF solution (5.24 mL, 5.24 mmol) was added to the solution, followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1), followed by crystallization from ethanol to obtain Compound 14 (0.579 g, yield 83%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)
  5. customfollowed by crystallization from ethanol

Sources & evidence

ORD record
ord-49e0a2ae2ae548328c6e1a05efcf0686
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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