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

HRID 1009731Notes

Reaction equation

HRID 1009731 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-6afb92396f814c81b332265e0db1aeba
Source dataset
uspto-grants-2011_07
Patent number
US07973165B2

Reaction notes

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