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Chemistry
Organic Building Blocks
Aryls
1-(2,4-Difluorophenyl)-4-iodo-1H-pyrazolo[3,4-b]pyridine
Chemistry
Organic Building Blocks
Heterocyclic Building Blocks
Aryls
Fluorinated Building Blocks Iodides Other Aromatic Heterocycles

[ CAS No. 1356054-70-0 ] {[proInfo.proName]}

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Chemical Structure| 1356054-70-0
Chemical Structure| 1356054-70-0
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CAS No. :1356054-70-0 MDL No. :MFCD21607382
Formula : C12H6F2IN3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 357.10 Pubchem ID :-
Synonyms :

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* 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 [ 1356054-70-0 ]

[ 1356054-70-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 40594-30-7 ]
  • [ 153034-82-3 ]
  • [ 1356054-70-0 ]
  • [ 1356054-71-1 ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; at 180℃; for 76.33h;Inert atmosphere; capped; To a dry 16x100mm Chem-Glass reaction tube under 2 was added 2-fluoro- 4-iodonicotinaldehyde (5g, 19.92 mmol), (2,4-difluorophenyl)hydrazine (3.01g, 20.92 mmol) and anhydrous NMP (35 mL). The reaction mixture was flushed with argon, securely capped, stirred for 20 min at room temp, and then placed in a 180C oil bath for 4h. The reaction mixture was then allowed to stir at room temperature for 72h. The reaction mixture was diluted with EtOAc (1200 mL) and the organic layer was extracted with water (6 x 350 mL), brine (1 x 100 mL), dried over Na2S04, filtered, and evaporated to dryness. The residue was purified by Biotage Silica gel chromatography on a 300g Thompson Single Step silica cartridge using a linear gradient from 100% hexanes to 100% dichloromethane over 10 column volumes to give 4.53g (44.6%) of Intermediate 13 A, as a light yellow solid that contained 28% of the uncyclized hydrazone intermediate ((E)-3-((2-(2,4-difluorophenyl)hydrazono)methyl)-2-fluoro-4-iodopyridine). 'H NMR (500 MHz, CC13D) delta ppm 8.21 (1 H, d, J=4.58 Hz), 8.14 (1 H, s), 7.59-7.71 (2 H, m), 7.10 (2 H, td, J=7.55, 3.81 Hz). LC/MS (Condition A): T = 3.7 min, (M+H)+ 357.90.
In 1-methyl-pyrrolidin-2-one; at 20 - 180℃; for 76.33h;Inert atmosphere; Sealed vial; Intermediate 8D : 1 -(2,4-Difluorophenyl)-4-iodo- 1 H-pyrazolo [3 ,4-b]pyridine[00128] To a dry 16x100mm CHEMGLASS reaction tube under N2 was added 2- fluoro-4-iodonicotinaldehyde (5g, 19.92 mmol), (2,4-difluorophenyl)hydrazine (3.01g, 20.92 mmol) and anhydrous NMP (35 mL). The reaction mixture was flushed with argon, securely capped, stirred for 20 min at room temp, and then placed in a 180 C oil bath for 4h. The reaction mixture was then allowed to stir at room temperature for 72h. The reaction mixture was diluted with EtOAc (1200 mL) and the organic layer was extracted with water (6 x 350 mL), brine (1 x 100 mL), dried over Na2S04, filtered, and evaporated to dryness. The residue was purified by BIOTAGE Silica gelchromatography on a 300g Thompson Single Step silica cartridge using a linear gradient from 100% hexanes to 100% dichloromethane over 10 column volumes to give 4.53g (44.6%) of Intermediate 8D, as a light yellow solid that contained 28% of the uncyclized hydrazone intermediate ((E)-3 -((2-(2,4-difluorophenyl)hydrazono)methyl)-2-fluoro-4- iodopyridine). ¾ NMR (500 MHz, CDC13) delta 8.21 (1 H, d, J=4.58 Hz), 8.14 (1 H, s), 7.59-7.71 (2 H, m), 7.10 (2 H, td, J=7.55, 3.81 Hz). LC/MS (Condition A): T = 3.7 min, (M+H)+ 357.90.
Reference： [1]Patent: WO2012/9510,2012,A1 .Location in patent: Page/Page column 59; 60
[2]Patent: WO2012/64815,2012,A1 .Location in patent: Page/Page column 39-40

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