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[ CAS No. 1426530-70-2 ] {[proInfo.proName]}

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Chemical Structure| 1426530-70-2
Chemical Structure| 1426530-70-2
Structure of 1426530-70-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1426530-70-2 ]

CAS No. :1426530-70-2 MDL No. :MFCD29918631
Formula : C16H11BrFN3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 392.18 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1426530-70-2 ]

* 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 [ 1426530-70-2 ]

[ 1426530-70-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1019021-93-2 ]
  • [ 369-26-6 ]
  • [ 1426530-70-2 ]
YieldReaction ConditionsOperation in experiment
A mixture comprising 7-bromoimidazo[1 ,2-a]pyridine-3-carboxylic acid (13c )(1 .8 g, approximately 7.47 mmol) and thionyl chloride (10 mL, 137 mmol) under N2 was heated at reflux for 1 .5 hours. The reaction mixture was concentrated in vacuo and azeotroped with toluene. Methyl 3-amino-4-fluorobenzoate (7) (1 .263 g, 7.47 mmol) (pre-dried at 45 °C) was added followed by pyridine and the mixture was stirred at room temperature under N2 overnight. The reaction mixture was diluted with EtOAc and washed with H20. The resulting solid was collected by filtration. The filtrate was dried (MgS04) and concentrated in vacuo and triturated with ether to afford a cream solid. The solids were combined and dried at 45 °C to afford the title compound (33). 1 H NMR (400MHz, d6- DMSO) delta 10.3 (1 H, s), 9.4 (1 H, d), 8.6 (1 H, s), 8.3 (1 H, m), 8.2 (1 H, s), 7.9 (1 H, m), 7.5 (1 H, t), 7.4 (1 H, d), 3.9 (3H, s). MS m/z 392 (M+H)+.
To the solution of compound 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1) (1.26 Kg, 5.23 mol) in DMAC (15 L) was added dropwise SOCl2 (1.86 kg, 15.6 mol) at 10 °C in 30 min. To the resulting mixture warmed to 20°C was added compound <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (884 g, 5.23 mol) in DMAC (3.0 L) over 30 min. After addition, the reaction temperature went up to 30 °C. HPLC showed the reaction went to completion within 5 min. To the reaction mixture was added water (20 L) over 20 min. The mixture was filtered and dried under vacuum to afford the title compound as a white solid; 1 H NMR (400 MHz, DMSO-d6) delta 3.87 (s, 3 H) 7.57 (dd, J=7.28, 2.01 Hz, 1 H) 7.51 (dd, J=10.16, 8.66Hz, 1 H) 7.90 (td, J=4.33, 2.38 Hz, 1 H) 8.29 (m, 2H) 8.90 (s, 1 H) 9.43 (d, J=7.53 Hz, 1 H) 10.78 (s, 1 H) Rt 6.90 mins; MS m/z 394.0 {M+H}+; Method 10 min LC
Step 1 : 3-[(7-Bromo-imidazo[1 ,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic acid methyl esterTo the solution of compound 7-bromoimidazo[1 ,2-a]pyridine-3-carboxylic acid (Intermediate A step 3) (1 .26 Kg, 5.23 mol) in DMAC (15 L) was added dropwise SOCI2 (1.86 kg, 15.6 mol) at 10 °C in 30 min. To the resulting mixture warmed to 20°C was added compound <strong>[369-26-6]methyl 3-amino-4-fluorobenzoate</strong> (884 g, 5.23 mol) in DMAC (3.0 L) over 30 min. After addition, the reaction temperature went up to 30 °C. HPLC showed the reaction went to completion within 5 min. To the reaction mixture was added water (20 L) over 20 min. The mixture was filtered and dried under vacuum to afford the title compound as a white solid;1 H NMR (400 MHz, DMSO-cfe) delta 3.87 (s, 3 H) 7.57 (dd, J=7.28, 2.01 Hz, 1 H) 7.51 (dd, J=10.16, 8.66Hz, 1 H) 7.90 (td, J=4.33, 2.38 Hz, 1 H) 8.29 (m, 2H) 8.90 (s, 1 H) 9.43 (d, J=7.53 Hz,1 H) 10.78 (s, 1 H)Rt 6.90 mins; MS m/z 394.0 {M+H}+; Method 10 
  • 2
  • [ 1134327-98-2 ]
  • [ 1426530-70-2 ]
  • 3
  • [ 1020174-04-2 ]
  • [ 1426530-70-2 ]
  • [ 1426530-94-0 ]
YieldReaction ConditionsOperation in experiment
step 2: 4-Fluoro-3-[7-(2-methyl-2H-pyrazol-3-yl)-imidazo[1 ,2-a]pyridine-3-carbonyl]- amino}-benzoic acid3-[(7-Bromo-imidazo[1 ,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic acid methyl ester (step 1 )(1200 g, 3.060 mol), 1-methyl-3-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazole (commercially available) (764 g, 3.67 mol),PdCI2(dppf CH2Cl2 (75.0 g, 91.8 mmol) in dioxane (10 L) and aqueous Na2C03 (2 N, 4.6 L) were heated to reflux for 6 hr. The reaction mixture was cooled to 50 C and filtered. The filtrate was heated to reflux, to which was added AcOH (600 g, 10.0 mol) was added dropwise. During the course of addition solids came out of solution to give pale pink slurry. After addition the mixture was slowly cooled to RT and filtered. To the filter cake was added dioxane (20 L) followed by heating to reflux to obtain a solution. The solution was cooled to RTand filtered to provide the title compound as a white solid;1H NMR (400 MHz, DMSO-d6) delta 4.00 (s, 3 H) 6.67 (s, 1 H) 7.46 (t, J=9.41 Hz, 1 H) 7.40 (d, J=7.03 Hz, 1 H) 7.54 (s, 1 H) 7.85 (d, J=2.26 Hz, 1 H) 7.99 (s, 1 H) 8.28 (d, J=6.27 Hz, 1 H) 8.67 (s, 1 H) 9.47 (d, J=7.03Hz, 1 H) 10.35 (s, 1 H).Rt 5.40 mins; MS m/z 380.1 {M+H}+; Method 10 min LC
  • 4
  • C8H4BrClN2O [ No CAS ]
  • [ 369-26-6 ]
  • [ 1426530-70-2 ]
  • 5
  • [ 1019021-93-2 ]
  • [ 1426530-70-2 ]
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