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[ CAS No. 948883-29-2 ] {[proInfo.proName]}

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Chemical Structure| 948883-29-2
Chemical Structure| 948883-29-2
Structure of 948883-29-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 948883-29-2 ]

CAS No. :948883-29-2 MDL No. :MFCD13183211
Formula : C10H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 185.18 Pubchem ID :-
Synonyms :

Safety of [ 948883-29-2 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 948883-29-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 948883-29-2 ]

[ 948883-29-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 136117-69-6 ]
  • [ 75-05-8 ]
  • [ 948883-29-2 ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With sodium hydride In toluene; mineral oil at 80℃; Stage #2: acetonitrile In toluene at 80℃; Stage #3: With hydrogenchloride In water; toluene General procedure for aryl/heteroaryl β-ketonitrile synthesis (Al):[0149] Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.[0150] To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 80 °C and then dry CH3CN was added dropwise (1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[0151] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2 N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM. [0152] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; 3-Imidazo[l, 2-aJpyridin- 6-yl-3-oxo-propionitrile[0159] The product was obtained starting from imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester according to general procedure Al :Yield 39%C10H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=O.23, 100% (3 min method)1H-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (1H, m), 8.07 (1H, s), 9.40 (s, 1H).
Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate; acetonitrile With sodium hydride In toluene at 80℃; for 18h; Stage #2: With hydrogenchloride; water In toluene at 20℃; To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 800C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.
Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With sodium hydride In toluene; mineral oil at 80℃; Heating / reflux; Stage #2: acetonitrile In toluene; mineral oil at 80℃; for 18h; Stage #3: With hydrogenchloride In water Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 80 0C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[00164] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.[00165] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; The product was obtained starting from imidazo[l,2-a]pyridine-6- carboxylic acid methyl ester according to general procedure AlYield 39%Ci0H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=0.23, 100% (3 min method)IH-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (IH, m), 8.07 (IH, s), 9.40 (s,IH).
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