Cesium carbonate → HCID 86648129, compound

HRID 2388237Notes

Reaction equation

HRID 2388237 reaction equation
[OH:1][C:2]1[C:3]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]=2[C:5]([C:13]#[C:14][Si](C)(C)C)=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+]>CCO.C(Cl)Cl>[C:13]([C:5]1[C:4]2[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:20][O:21][C:3]=2[C:2]([OH:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)#[CH:14]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 67532332HCID 67532332, compound

Product 1

HCID 86648129HCID 86648129, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Ethyl 7-hydroxy-3-phenyl-4-((trimethylsilyl)ethynyl)isoxazolo[4,5-c]pyridine-6-carboxylate (205 mg, 0.54 mmol) was dissolved in a 1:1 mixture of EtOH/CH2Cl2 (6 mL). Cesium carbonate (211 mg, 0.65 mmol) was added and the resulting slurry was stirred at room temperature for 14 h. The solvent was evaporated and the residue was partitioned between EtOAc (25 mL) and 1 M hydrochloric acid (25 mL). The aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over MgSO4 and concentrated to give 185 mg of the title compound. MS: (+) m/z 309.29 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EtOAc (25 mL) and 1 M hydrochloric acid (25 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a6a67227b89548ba83cd730041348b4d
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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