Water → HCID 10176480, compound

HRID 2080005Notes

Reaction equation

HRID 2080005 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[C:9](=[O:18])[NH:8][CH:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>C(O)C.C(N(CC)CC)C.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]2[CH:12]=[CH:13][O:18][C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 10890714HCID 10890714, compound

Product 1

HCID 10176480HCID 10176480, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

6Oxo-5-trimethylsilanylethynyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester described in Preparation Example P-3 (545 mg, 2.07 mmol) and copper(I)iodide (5.9 mg, 31 μmol) were suspended in ethanol (7 mL) and triethylamine (3 mL), and the mixture was stirred at 75° C. for 20 hours. The reaction mixture was cooled to room temperature, then, potassium carbonate (572 mg, 4.14 mmol) was added to the reaction mixture, which was further stirred at 75° C. for 5 hours. The reaction mixture was cooled to 0° C., then, water was added, the precipitated solid was filtered, and the title compound (303 mg) was obtained as a brown solid. In addition, ethyl acetate was added to the mother liquor for extraction, the organic layer was washed with brine, then, dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (33 mg, 0.17 mmol) was obtained as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-76e08aa410ba4e879f87f439fa5d48bf
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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