Ethyl Acetate → HCID 11030983, compound

HRID 876835Notes

Reaction equation

HRID 876835 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:12]2[CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(OCC)(=O)C>C1COCC1>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:12]2[CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 67305706HCID 67305706, compound

Product 1

HCID 11030983HCID 11030983, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-((tert-butyldimethylsilyloxy)methyl)pyrazolo[1,5-a]pyridine-3-carboxylate (Y-5) (2.9 g, 9.1 mmol) in anhydrous THF (20 mL) was added TBAF (3.5 g, 13.7 mmol). The reaction mixture was stirred at room temperature for 10 min, then treated with ethyl acetate (50 mL). The resulting mixture was washed with brine, dried over Na2SO4 and concentrated to afford the title compound (1.9 g).

Workup

  1. washThe resulting mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-30f21adc6b744167b0a4186329d0e984
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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