Potassium Carbonate → HCID 24738829, compound

HRID 731642Notes

Reaction equation

HRID 731642 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[C:19]([C:21]#[C:22][Si](C)(C)C)[CH:18]=[CH:17][N:16]2[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CO.[Cl-].[Na+].O>[C:21]([C:19]1[CH:18]=[CH:17][N:16]2[CH:27]=[C:13]([C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])[N:14]=[C:15]2[CH:20]=1)#[CH:22]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 69062824HCID 69062824, compound

Product 1

HCID 24738829HCID 24738829, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The mixture was then poured into cold hydrochloric acid (1 M) and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a yellow oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30) afforded 2-(5-methyl-3-phenyl-isoxazol-4-yl)-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridine (86 mg, 82%) which was obtained as a yellow foam. MS: m/e=372.1 [M+H]+. Then 2-(5-methyl-3-phenyl-isoxazol-4-yl)-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridine (81 mg, 0.22 mmol) was dissolved in methanol (1 mL), a spatula tip of potassium carbonate was added at 0° C. and the reaction mixture was stirred at room temperature for 2 h. The mixture was then poured into brine and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a brown oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30) afforded the title compound (53 mg, 81%) which was obtained as a yellow foam. MS: m/e=300.3 [M+H]+.

Workup

  1. customwas obtained as a yellow foam
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto leave a brown oil
  7. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-0a32bdb0bc794ecbac8337a0f8beafba
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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