Methanol → 5-(1H-indol-2-yl)oxazole

HRID 1038419노트

반응식

HRID 1038419 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=[O:11].CO.C1(C)C=CC(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[O:11][CH:25]=[N:24][CH:23]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 96389Indole-2-carboxaldehydeHCID 161915Tosylmethyl isocyanide

생성물 1

HCID 8520455-(1H-indol-2-yl)oxazole수율 79.8%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

To a 100 mL round-bottom flask was added 1H-indole-2-carbaldehyde 18 (1.52 g, 10.48 mmol), methanol (50 mL), p-toluene sulfonylmethyl isocyanide (2.25 g, 11.52 mmol), followed by potassium carbonate (1.86 g, 13.45 mmol). The reaction mixture was stirred at reflux for about 1.5 hour and followed by TLC. The solvent was then evaporated and saturated aq.NaHCO3 was added. The resultant suspension was extracted with CH2Cl2 (3×30 mL). Combined organic layers were washed with brine, dried (anhydrous Na2SO4), and concentrated to leave a yellow solid. Crude product was further purified by silica-column chromatographed (Biotage) using Acetone:Hexane as an eluent to yield 5-(1H-indol-2-yl)oxazole 19 (1.54 g, 79% yield). MS (ES) m/z 185 (M+H+).

후처리

  1. temperatureat reflux for about 1.5 hour
  2. customThe solvent was then evaporated
  3. additionNaHCO3 was added
  4. extractionThe resultant suspension was extracted with CH2Cl2 (3×30 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. customCrude product was further purified by silica-column
  10. customchromatographed (Biotage)

출처 및 근거

ORD 기록
ord-9485366df5264b12a05206938a86aac6
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551992B2

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