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Chemical Structure| 1101120-53-9 Chemical Structure| 1101120-53-9

Structure of 1101120-53-9

Chemical Structure| 1101120-53-9

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Product Details of [ 1101120-53-9 ]

CAS No. :1101120-53-9
Formula : C8H5BrN2O
M.W : 225.04
SMILES Code : O=CC1=C2C=C(Br)C=CN2N=C1
MDL No. :MFCD21365053

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Application In Synthesis of [ 1101120-53-9 ]

* 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 [ 1101120-53-9 ]

[ 1101120-53-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1060812-84-1 ]
  • [ 68-12-2 ]
  • [ 1101120-53-9 ]
YieldReaction ConditionsOperation in experiment
96% General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40percent aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 °C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.
  • 2
  • [ 1060812-84-1 ]
  • [ 3724-43-4 ]
  • [ 1101120-53-9 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane; at 44℃; To a solution of <strong>[1060812-84-1]5-bromopyrazolo[1,5-a]pyridine</strong> (175 mg, 0.89 mmol) in DCM (6 mL) was added (chloromethylene)dimethyliminium chloride (632 mg, 3.56 mmol). The reaction was stirred at 44° C. overnight, and concentrated in vacuo. The residue was dissolved in saturated NaHCO3 aqueous solution (25 mL) and the resulted mixture was then extracted with EtOAc (25 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid (225 mg, 100percent). [0332] MS (ESI, pos. ion) m/z: 225.0 [M+H]+.
  • 3
  • [ 1101120-53-9 ]
  • [ 1101120-80-2 ]
  • [ 302-15-8 ]
  • [ 1101119-38-3 ]
YieldReaction ConditionsOperation in experiment
64% With 2,6-dimethylpyridine; In methanol; for 0.5h; General procedure: Methylhydrazine sulfate (1.2 eq.) and 2,6-lutidine (5 eq.) were added to a solution of aldehyde (1 eq.) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 eq.) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.
 

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