Potassium Carbonate → N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

HRID 1962851Notes

Reaction equation

HRID 1962851 reaction equation
[C:1]([NH:5][C:6](=[O:27])[CH:7]([S:25][CH3:26])[O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([C:19]#[C:20][Si](C)(C)C)=[CH:12]2)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[C:1]([NH:5][C:6](=[O:27])[CH:7]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([C:19]#[CH:20])=[CH:12]2)[S:25][CH3:26])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59565338N-tert-Butyl-2-methylsulfanyl-2-(3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetamide

Product 1

HCID 59565325N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamideYield 70.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-tert-Butyl-2-methylsulfanyl-2-(3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetamide (215 mg) in methanol (5 ml) was treated with potassium carbonate (18 mg) at room temperature. The reaction mixture was stirred for 1 h. The reaction mixture was diluted with ethyl acetate and washed with 30 ml sat. aq. sodium hydrogen carbonate. The aqueous layer was extracted with 3×50 ml ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 6:4) to give N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (125 mg) as brownish solid.

Workup

  1. washwashed with 30 ml sat. aq. sodium hydrogen carbonate
  2. extractionThe aqueous layer was extracted with 3×50 ml ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (heptane/ethyl acetate 6:4)

Sources & evidence

ORD record
ord-a2dec608e9ce476b8336dca96737ffdd
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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