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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methyl iodide → 3-(5-((methylthio)methyl)furan-2-yl)pyridine

HRID 1913349
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HRID 1913349 반응식
[C:1](=O)([S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)C.C[O-].[Na+].CI.C(=O)(O)[O-].[Na+]>CO>[CH3:1][S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1
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참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 11993872S-(5-(Pyridin-3-yl)furan-2-yl)methyl ethanethioate

생성물 1

HCID 119938733-(5-((methylthio)methyl)furan-2-yl)pyridine수율 54%

시약·촉매·용매 1

HCID 887Methanol
용매
3회

실험 절차

(See FIG. 7.) To a solution of 13 (27 mg, 0.12 mmol) in anhydrous CH3OH (3 mL) at 0° C. under argon was added a solution of sodium methoxide (15 mg, 0.28 mmol) in anhydrous CH3OH (1 mL) dropwise, over 10 min and the resultant solution was stirred for 30 min. To the solution was added methyl iodide (17 μL, 0.28 mmol) in anhydrous CH3OH (1 mL) dropwise over 1 min and the resultant solution was stirred for 30 min. The reaction was stopped by the addition of aqueous sodium bicarbonate (satd. soln., 10 mL). The CH3OH was removed in vacuo and the aqueous fraction was extracted with EtOAc (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.2) to afford the title compound 15 (13 mg, 54% yield) as an off white solid: mp=67-68° C.; 1H NMR (CDCl3) δ 8.90 (br s, 1H), 8.46 (m, 1H), 7.90 (m, 1H), 7.29 (m, 1H), 6.66 (d, J=3.3 Hz, 1H), 6.29 (d, J=3.3 Hz, 1H), 3.74 (s, 2H), 2.14 (s, 3H); LRMS (ESI) m/z calcd for C11H12NOS [M+H]+ 206. found 206.

후처리

  1. customThe CH3OH was removed in vacuo
  2. extractionthe aqueous fraction was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.2)

출처 및 근거

ORD 기록
ord-3d710a995b4e42999e5f51094cc7427a
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609708B2

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