Potassium Carbonate → 2-Furan-3-yl-6-methoxy-1H-indole

HRID 2409958ノート

反応式

HRID 2409958 の反応式
FC(F)(F)C([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1I)=O.[O:17]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][Si](C)(C)C)=[CH:18]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>[O:17]1[CH:21]=[CH:20][C:19]([C:22]2[NH:5][C:6]3[C:7]([CH:23]=2)=[CH:8][CH:9]=[C:10]([O:12][CH3:13])[CH:11]=3)=[CH:18]1

参加物

11

反応物 4

HCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 16217672[2-(Furan-3-yl)ethynyl]trimethylsilaneHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamide

生成物 1

HCID 867032792-Furan-3-yl-6-methoxy-1H-indole収率 68.3%

試薬・触媒・溶媒 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 2,2,2-trifluoro-N-(2-iodo-5-methoxyphenyl)acetamide (1.00 g), furan-3-ylethynyltrimethylsilane (714 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 (422 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 6.51-6.56 (1H, m), 6.64-6.69 (1H, m), 6.78 (1H, dd, J=2.3, 8.5 Hz), 6.84-6.90 (1H, m), 7.42-7.51 (2H, m), 7.67-7.73 (1H, m), 7.78-8.13 (1H, br).

後処理

  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)

出典と根拠

ORDレコード
ord-7f70ba1d5b3742818b70528496818d22
出典データセット
uspto-grants-2014_08
特許番号
US08815903B2

反応ノート

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