Potassium Carbonate → (S)-5-ethynyl-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391518노트

반응식

HRID 391518 반응식
[CH3:1][S@:2](=[O:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[N:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[C:11]([C:9]1[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=1)[C:4]([N:3]=[S@@:2]([CH3:1])(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17])#[CH:12]

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 24953135(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

생성물 1

HCID 24953136(S)-5-ethynyl-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of (S)—N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (806 mg, 2.3 mmol) in 70 mL THF/methanol (1:1 ratio) at room temperature was degassed with argon. The solution was cooled to 0° C. and K2CO3 (937 mg, 6.8 mmol) added. After 5 minutes the solution was decanted from the solids and partitioned between EtOAc and H2O. The EtOAc layer was washed with brine, dried with anhydrous Na2SO4 and concentrated. The brown oil was purified by chromatography (silica gel, CHCl3/EtOAc) to the title compound as a thick pale orange oil (630 mg, 98%).

후처리

  1. customAfter 5 minutes the solution was decanted from the solids
  2. custompartitioned between EtOAc and H2O
  3. washThe EtOAc layer was washed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe brown oil was purified by chromatography (silica gel, CHCl3/EtOAc) to the title compound as a thick pale orange oil (630 mg, 98%)

출처 및 근거

ORD 기록
ord-61b1b24e84a74a3ea1a076a97294d084
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383825B2

반응 노트

불러오는 중…