Potassium Carbonate → 6-Methoxy-2-(5-methylthiophen-3-yl)-1H-indole

HRID 2409956노트

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HRID 2409956 반응식
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1I)=O.C[Si](C)(C)C#C[C:21]1[CH:25]=[C:24]([CH3:26])[S:23][CH:22]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.[Cl-].[Na+].O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(#N)C.C(N(CC)CC)C>[CH3:13][O:12][C:10]1[CH:11]=[C:6]2[C:7]([CH:2]=[C:3]([C:21]3[CH:25]=[C:24]([CH3:26])[S:23][CH:22]=3)[NH:5]2)=[CH:8][CH:9]=1

참가 물질

11

반응물 4

HCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamideHCID 86703276Trimethyl(5-methylthiophen-3-ylethynyl)silane

생성물 1

HCID 867032776-Methoxy-2-(5-methylthiophen-3-yl)-1H-indole수율 63.7%

시약·촉매·용매 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 57417360Sodium chloride; water용매

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온도
50 °C

실험 절차

To a mixture of 2,2,2-trifluoro-N-(2-iodo-5-methoxyphenyl)acetamide (1.00 g), trimethyl(5-methylthiophen-3-ylethynyl)silane (845 mg), bis(triphenylphosphine) palladium(II) dichloride (61 mg), copper(I) iodide (33 mg), triethylamine (0.81 mL), and acetonitrile (15 mL) was added tetrabutylammonium fluoride in tetrahydrofuran solution (1 mol/L, 4.4 mL) at 50° C. This mixture was stirred at 50° C. for 1 hour. Then, potassium carbonate (801 mg) was added thereto, followed by stirring at 50° C. overnight. To the reaction mixture was added saturated brine, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (449 mg). 1H-NMR (CDCl3) δ ppm: 2.53 (3H, d, J=1.0 Hz), 3.86 (3H, s), 6.53-6.59 (1H, m), 6.77 (1H, dd, J=2.3, 8.6 Hz), 6.84-6.89 (1H, m), 7.01-7.11 (2H, m), 7.46 (1H, d, J=8.6 Hz), 7.94-8.16 (1H, br).

후처리

  1. stirringby stirring at 50° C. overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-4094b8e81a804684b69062bf461ebb0f
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815903B2

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