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Sodium Bicarbonate → 2-Cyclopropyl-5-(2-methyl-4-trimethylsilanylethynyl-imidazol-1-yl)-pyridine

HRID 1009731
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HRID 1009731 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:10]=[C:9]2[CH3:19])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[Cl-].[CH:26]1([Zn+])[CH2:28][CH2:27]1>C1COCC1>[CH:26]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:12]=[C:11]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:10]=[C:9]3[CH3:19])=[CH:4][N:3]=2)[CH2:28][CH2:27]1
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 865953252-Chloro-5-(2-methyl-4-trimethylsilanylethynyl-imidazol-1-yl)-pyridineHCID 178479835HCID 178479835, 화합물

생성물 1

HCID 673044862-Cyclopropyl-5-(2-methyl-4-trimethylsilanylethynyl-imidazol-1-yl)-pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Chloro-5-(2-methyl-4-trimethylsilanylethynyl-imidazol-1-yl)-pyridine (425 mg, 1.47 mmol) were dissolved in 0.4M cyclopropylzinc chloride in THF (7.33 mL, 0.4M in THF) and tetrakis(triphenylphosphin)palladium (34 mg, 0.03 mmol) were added. The reaction mixture was refluxed for 16 hrs and poured into 50 mL sat. sodium bicarbonate solution. The mixture and extracted three times with ethyl acetate (50 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->1:1 gradient) and the desired product was obtained as a light yellow solid (395 mg, 91%), MS: m/e=296.2 (M+H+).

후처리

  1. temperatureThe reaction mixture was refluxed for 16 hrs
  2. extractionThe mixture and extracted three times with ethyl acetate (50 mL each)
  3. dry with materialThe combined organic extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->1:1 gradient)

출처 및 근거

ORD 기록
ord-6afb92396f814c81b332265e0db1aeba
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07973165B2

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