Sodium Bicarbonate → HCID 10469429, compound

HRID 860156Notes

Reaction equation

HRID 860156 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=3)[N:10]=[C:9]2[CH3:22])[N:3]=1.[CH3:23][Zn]C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:23][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=3)[N:10]=[C:9]2[CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10335523HCID 10335523, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 10469429HCID 10469429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-6-[2-methyl-4-(2-methyl-pyridin-4-ylethynyl)-imidazol-1-yl]-pyrazine (27)(300 mg, 0.968 mmol) was dissolved in 5 mL dry tetrahydrofuran. Dimethylzinc (1.2 mL, 2M in toluene) and tetrakis(triphenylphosphin)palladium (23 mg, 0.02 mmol) were added. The reaction mixture was refluxed for 2 h and poured into 50 mL sat. sodium bicarbonate solution. The mixture was 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 (dichloromethane/methanol 100:0→90:10 gradient) and the desired product was obtained as a light yellow solid (240 mg, 85%), MS: m/e=290.1 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionThe mixture was 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 (dichloromethane/methanol 100:0→90:10 gradient)

Sources & evidence

ORD record
ord-9ce91d2aca854d09a6f25c0dc1bdf233
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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