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Chemistry
Organic Building Blocks
Iodides
3-Iodo-1H-pyrazolo[4,3-b]pyridine
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[ CAS No. 633328-40-2 ] {[proInfo.proName]}

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Chemical Structure| 633328-40-2
Chemical Structure| 633328-40-2
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Quality Control of [ 633328-40-2 ]

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Product Details of [ 633328-40-2 ]

CAS No. :633328-40-2 MDL No. :MFCD10696864
Formula : C6H4IN3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 245.02 Pubchem ID :-
Synonyms :

Safety of [ 633328-40-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 633328-40-2 ]

* 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 [ 633328-40-2 ]

[ 633328-40-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 272-52-6 ]
  • [ 633328-40-2 ]
YieldReaction ConditionsOperation in experiment
60.8% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere; To a solution of 1H-pyrazolo[4,3-b] pyridine (800.0 mg, 6.7 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added KOH (1.1 g, 20.2 mmol, 3.0 eq.) and ?2 (3.4 g, 13.4 mmol, 2.0 eq.) under nitrogen at a The mixture was stirred for 2 h, then diluted with ice water, extracted with EA (30 mL x 3). The combined organic layers were washed with aqueous Na2S2O3 and brine, dried over anhydrous Na2SO4, concentrated in vacuum. The residue was purified by column chromatography (DCMIMeOH = 40:1) to provide 3-iodo-1H- <strong>[272-52-6]pyrazolo[4,3-b]pyridine</strong> (1.0 g, 60.8percent).
60.8% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; for 2h;Inert atmosphere; To a solution of lH-pyrazolo[4,3-b] pyridine (800.0 mg, 6.7 mmol, 1.0 eq.) in anhydrous DMF (10 mL) were added KOH (1.1 g, 20.2 mmol, 3.0 eq.) and I2 (3.4 g, 13.4 mmol, 2.0 eq.) under nitrogen at r. . The mixture was stirred for 2 h, then diluted with ice water, extracted with EA (30 mL chi 3). The combined organic layer was washed with aqueous Na2S203 and brine, dried over anhydrous Na2S04, concentrated under vacuum. The residue was purified by column chromatography (DCM/MeOH = 40: 1) to provide 3-iodo-1H-pyrazolo[4,3-bjpyridine (1.0 g, 60.8percent).
57% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 25℃; for 16h; A mixture of <strong>[272-52-6]1H-<strong>[272-52-6]pyrazolo[4,3-b]pyridine</strong></strong> (10 g, 83.95 mmol, 1.00 equiv), potassium hydroxide (16.9 g, 301.22 mmol, 3.60 equiv), and iodine(42.7 g, 168.24 mmol, 2.00 equiv) in DMF (150 mL)was stirred for 16 hours at 25 °C. The resulting solution was diluted with water, extracted with ethyl acetate, washed with sodium bisulfate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:3). This resulted in the title compound (11.7 g, 57percent) as a yellow solid. LC-MS (ES, mlz): 246 [M+H1.
Reference： [1]Patent: WO2017/98328,2017,A2 .Location in patent: Paragraph 00225
[2]Patent: WO2018/229543,2018,A2 .Location in patent: Paragraph 00196
[3]Patent: WO2015/25025,2015,A1 .Location in patent: Page/Page column 362; 363
[4]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6998 - 7003
[5]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1852 - 1856
  • 2
  • [ 633328-40-2 ]
  • [ 2557-78-0 ]
  • [ 1234572-71-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In ethylene glycol; isopropyl alcohol at 130℃; for 20h; Inert atmosphere; 1A Example 1A 3-[(2-Fluorophenyl)sulphanyl]-1H-pyrazolo[4,3-b]pyridine Under an atmosphere of argon, 4.84 ml (86.77 mmol) of 1,2-ethanediol, 250 ml of 2-propanol and 11.12 g (86.77 mmol) of 2-fluorothiophenol were added to 10.63 g (43.38 mmol) of 3-iodo-1H-pyrazolo[4,3-b]pyridine, 1.24 g (6.51 mmol) of copper(I) iodide and 12.0 g (86.77 mmol) of potassium carbonate, and the mixture was stirred at 130° C. for 20 hours. The salts were filtered off with suction, silica gel was added to the filtrate, the mixture was concentrated and the residue was chromatographed on a silica gel column using a gradient of cyclohexane/ethyl acetate=10:1 to 1:1. This gave 11.55 g (98% of theory) of the product in a purity of 90% (HPLC). LC-MS (Method 6): Rt=0.83 min MS (ESIpos): m/z=246.1 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): δ=6.9-7.1 (m, 2H), 7.2-7.3 (m, 2H), 7.46 (dd, 1H), 8.10 (d, 1H), 8.55 (d, 1H), 13.88 (broad s, 1H).
Reference： [1]Current Patent Assignee: BAYER AG - US2012/29002, 2012, A1 Location in patent: Page/Page column 16

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