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Chemical Structure| 1082040-63-8 Chemical Structure| 1082040-63-8
Chemical Structure| 1082040-63-8

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3-Iodo-1H-pyrazolo[3,4-c]pyridine

CAS No.: 1082040-63-8

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Cat. No.: A247865 Purity: 98%

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Product Details of [ 1082040-63-8 ]

CAS No. :1082040-63-8
Formula : C6H4IN3
M.W : 245.02
SMILES Code : IC1=NNC2=C1C=CN=C2
MDL No. :MFCD11845480
Boiling Point : No data available
InChI Key :BFJMHTOBRRZELQ-UHFFFAOYSA-N
Pubchem ID :53399429

Safety of [ 1082040-63-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis [ 1082040-63-8 ]

* 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 [ 1082040-63-8 ]

[ 1082040-63-8 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 5292-43-3 ]
  • [ 1082040-63-8 ]
  • [ 1386457-65-3 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h; To a solution of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> (6.0 g, 24.5 mmol, 1.0 eq.) and K2C03 (4.0 g, 29.4 mmol, 1.2 eq.) in DMF (40 mL) was added tert-butyl 2-bromoacetate (4.78 g, 24.5 mmol, 1.0 eq.). The resulting mixture was stirred at r.t. for 2 h, then poured into water (200 mL), extracted with EtOAc (200 mL x 3). The combined organic layers were dried and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=3 :1) to providetert-butyl 2-(3 -iodo- 1 H-pyrazolo[3 ,4-c]pyridin- 1 -yl)acetate as a yellow oil (6.0 g, 68.0%).
68% With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h; To a solution of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> (6.0 g, 24.5 mmol, 1.0 eq.) and K2C03 (4.0 g, 29.4 mmol, 1.2 eq.) in DMF (40 mL) was added tert-butyl 2- bromoacetate (4.78 g, 24.5 mmol, 1.0 eq.). The resulting mixture was stirred at rt for 2 h, poured into water (200 mL), and extracted with EtOAc (200 mL x 3). The combined organic layers were dried and concentrated. The residue was purified by column chromatography (PE/EtOAc=3:1) to PROVIDE tert-butyl 2-(3-iodo-1H-pyrazolo[3,4- c]pyridin-1-yl)acetate as a yellow oil (6.0 g, 68.0% yield).
68% With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h; To a solution of 3-iodo-lH-pyrazolo[3,4-c]pyridine (6.0 g, 24.5 mmol, 1.0 eq.) and K2C03 (4.0 g, 29.4 mmol, 1.2 eq.) in DMF (40 mL) was added tert-butyl 2-bromoacetate (4.78 g, 24.5 mmol, 1.0 eq.). The resulting mixture was stirred at r.t. for 2 h, then poured into water (200 mL), extracted with EtOAc (200 mL x 3). The combined organic layers were dried and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=3: l) to provide tert-butyl 2-(3-iodo-lH-pyrazolo[3,4- c]pyridin-l-yl)acetate as a yellow oil (6.0 g, 68.0% yield).
With potassium carbonate; In acetonitrile; at 20.0℃; for 2.0h;Reflux; To a suspension of 3-iodo-1 H-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in acetonitrile (50 mL) was added tert-butyl bromoacetate (4.06 mL, 27.5 mmol) dropwise at RT and the resulting mixture was heated to reflux for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was purified by flash column chromatography on silica gel (gradient EtOAc/c-hexane 1 :4, then 1 :2, then 1 :1). MS (LC/MS): 360.0 [M+H]+; tR (HPLC conditions k): 2.93 min.
With potassium carbonate; In acetonitrile; for 2.0h;Reflux; B. Tert-butyl 2-(3-iodo-I H-pyrazolo[3,4-c]pyridi n-I -yI)acetateTo a suspension of 3-iodo-1 H-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added tert-butyl bromoacetate (4.06 mL, 27.5 mmol) dropwise at RT and the resulting mixture was heated to reflux for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was purified by flash column chromatography on silica gel (EtOAcc-hexane 1:4, to 1:2, to 1:1) to give the title compound. MS (LCMS): 360.0 [M+H]+; tR (HPLC conditions d): 2.93 mm.
With potassium carbonate; In acetonitrile; for 2.0h;Reflux; B. Tert-butyl 2-(3-iodo-I H-pyrazolo[3,4-c]pyridi n-I -yI)acetateTo a suspension of 3-iodo-IH-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added dropwise at RT tert-butyl 2- bromoacetate (4.06 mL, 27.5 mmol). The resulting mixture was refluxed for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated and purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1, then 2:1, then 1:1) to afford the title compound. MS (LC/MS): 360.0 [M+H]+; tR (HPLC conditions d): 2.93 mm.
With potassium carbonate; In acetonitrile; for 2.0h;Reflux; To a suspension of 3-iodo-1 H-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added tert-butyl bromoacetate (4.06 mL, 27.5 mmol) dropwise at RT and the resulting mixture was heated to reflux for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was purified by flash column chromatography on silica gel (EtOAc/c-hexane 1 :4, to 1 :2, to 1 :1 ) to give the title compound. MS (LC/MS): 360.0 [M+H]+; tR (HPLC conditions d): 2.93 min.
With potassium carbonate; In acetonitrile; for 2.0h;Reflux; To a suspension of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added tert-butyl 2-bromoacetate (4.06 mL, 27.5 mmol) dropwise. The resulting mixture was heated to reflux for 2 h, cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated and the product was purified by flash column chromatography on silica gel (c-hexaneEtOAc 4:1 to 1:1). MS (LCMS): 360.0 [M+H]+; tR (H PLC conditions d): 2.93 mm.
With potassium carbonate; In acetonitrile; for 2.0h;Reflux; To a suspension of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added tert-butyl bromoacetate (4.06 mL, 27.5 mmol) dropwise at RT and the resulting mixture was heated to reflux for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was purified by flash column chromatography on silica gel (EtOAcc-hexane 1:4, to 1:2, to 1:1) to give the title compound. MS (LCMS): 360.0 [M+H]+; tR (HPLC conditions b): 2.93 mm.
With potassium carbonate; In acetonitrile; for 2.0h;Reflux; To a suspension of 3-iodo-1 H-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added dropwise at RT, tert-butyl 2-bromoacetate (4.06 mL, 27.5 mmol). The reaction mixture was refluxed for 2 h, cooled to RT and filtered. The solid was washed with CH3CN, the filtrate was concentrated and the product purified by flash column chromatography on silica gel (EtOAcc-hexane 1:4, then 1:2, then 1:1). MS (LCMS): 360.0 [M+H]+; tR (HPLC conditions d): 2.93 mm.

  • 2
  • [ 271-47-6 ]
  • [ 1082040-63-8 ]
YieldReaction ConditionsOperation in experiment
84% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; A suspension of 1H-pyrazolo[3,4-c]pyridine (300 mg, 2.52 mmol, 1.00 equiv), KOH (500 mg,8.91 mmol, 3.50 equiv), and diiodane (1.28 g, 5.04 mmol, 2.00 equiv) in DMF (10 mL) was stirredovernight at room temperature. The reaction was quenched by water, extracted with ethyl acetate,dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified bya silica gel column with ethyl acetate/petroleum ether (1:1) to give the title compound (577 mg,84%) as a yellow solid. LC-MS (ES, mlz): 246 [M+H].
73% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 3.0h; To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF(40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), ?2 (7.9 g, 33.6 mmol, 1.0 eq.). Theresulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collectedsolid was dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 %).
73% With iodine; potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 3.0h; To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF (40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.) and ?2 (7.9 g, 33.6 mmol, 1.0 eq.). The resulting mixture was stirred at rt for 3 h, then diluted by H20 and filtered. The solid was collected and dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 % yield).
73% With iodine; potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 3.0h; To a solution of lH-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF (40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), I2 (7.9 g, 33.6 mmol, 1.0 eq.). The resulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collected solid was dried to give 3-iodo-lH- pyrazolo[3,4-c]pyridine (6.0 g, 73.0 % yield).
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; To a solution of 1 H-pyrazolo[3,4-c]pyridine [271-47-6 ] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, then dried (Phase separator) and concentrated under vacuum. MS (LC/MS): 246.0 [M+H]+; tR (HPLC conditions k): 0.48 min.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; A. 3-Iodo-I H-pyrazolo[3,4-c]pyridineTo a solution of 1 H-pyrazolo[3,4-c]pyridine [27 1-47-6 1(4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. MS (LCMS): 246.0 [M+H]+; tR (HPLC conditions d): 0.48 mm.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; A. 3-lodo-1 H-pyrazolo[3,4-c]pyridineTo a solution of IH-pyrazolo[3,4-c]pyridine [271-47-6 ] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (phase separator) and concentrated. MS (LC/MS): 246.0 [M+H]+; tR (H PLC conditions d): 0.48 mm.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; To a solution of 1 H-pyrazolo[3,4-c]pyridine [271-47-6 ] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. MS (LC/MS): 246.0 [M+H]+; tR (HPLC conditions d): 0.48 min.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; To a solution of 1H-pyrazolo[3,4-c]pyridine [271-47-6] (4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water and extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried (phase separator) and concentrated to afford the title compound. MS (LCMS): 246.0 [M+H]+; tR (H PLC conditions d): 0.48 mm.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h;Inert atmosphere; To a solution of 1H-pyrazolo[3,4-c]pyridine [271-47-6 1(4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted (3x) with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. MS (LCMS):246.0 [M+H]+; tR (H PLC conditions b): 0.48 mm.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; To a solution of 1H-pyrazolo[3,4-c]pyridine [271-47-61(4.00 g, 33.6 mmol) in DMF (50 mL) were added iodine (12.8 g, 50.4 mmol) and potassium hydroxide (4.70 g, 84.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was diluted with 10% sodium thiosulfate and water, then extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried (phase separator) and concentrated. MS (LCMS): 246.0 [M+H]+; tR (H PLC conditions d):0.48 mm.

  • 6
  • [ 1082040-63-8 ]
  • [ 5188-07-8 ]
  • [ 1538626-63-9 ]
YieldReaction ConditionsOperation in experiment
50% With copper(l) iodide; In dimethyl sulfoxide; at 150.0℃;Inert atmosphere; Step 4: synthesis of 3-methanesulfonyl- 1 H-pyrazolo [3 ,4-c]pyridine To a solution of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> 3 (9.5 g, 38.8 mmol) in DMSO (20 mL) was added aq. MeSNa (wt. 20%, 40 mL, 116 mmol), followed by CuT (270 mg, 1.94 mmol). The mixture was degas sed and refilled with nitrogen. The reaction was heated at 150 C overnight. After cooled to RT, the volatiles were removed and the residue was purified by column (PE/EtOAc=2/1 to 1/1) to give 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (3.2 g, yield: 50%) asa yellow solid. MS obsd. (ESIj [(M+H)?i 166.0.To a solution of 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (10 g, 60.6 mmol) in DMF (100 mL) was added oxone (37 g, 121.2 mmol.) in portions. The reaction mixture was stirred at RT. After the reaction completed, water (100 mL) was added. The reaction was quenched carefully by addition of Na2503 and Na2CO3. The solid was filtered off and washed with MeOH (300 mL).The filtrate was concentrated under vacuum and the residue was purified by chromatography on silica gel column (DCM/MeOH=20/1) to give 3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (10.7g, yield: 90%) as a yellow solid. MS obsd. (ESIj [(M+H)?i 198.0.
50% With copper(l) iodide; In water; dimethyl sulfoxide; at 150.0℃;Inert atmosphere; Step 4: synthesis of 3-methanesulfonyl-1H-pyrazolo[3,4-c]pyridine To a solution of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> 3 (9.5 g, 38.8 mmol) in DMSO (20 mL) was added aq. MeSNa (wt. 20%, 40 mL, 116 mmol), followed by CuI (270 mg, 1.94 mmol). The mixture was degassed and refilled with nitrogen. The reaction was heated at 150 C. overnight. After cooled to RT, the volatiles were removed and the residue was purified by column (PE/EtOAc=2/1 to 1/1) to give 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (3.2 g, yield: 50%) as a yellow solid. MS obsd. (ESI+) [(M+H)+] 166.0. To a solution of 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (10 g, 60.6 mmol) in DMF (100 mL) was added oxone (37 g, 121.2 mmol.) in portions. The reaction mixture was stirred at RT. After the reaction completed, water (100 mL) was added. The reaction was quenched carefully by addition of Na2SO3 and Na2CO3. The solid was filtered off and washed with MeOH (300 mL). The filtrate was concentrated under vacuum and the residue was purified by chromatography on silica gel column (DCM/MeOH=20/1) to give 3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (10.7 g, yield: 90%) as a yellow solid. MS obsd. (ESI+) [(M+H)+] 198.0.
50% With copper(l) iodide; In water; dimethyl sulfoxide; at 150.0℃;Inert atmosphere; To a solution of <strong>[1082040-63-8]3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> 3 (9.5 g, 38.8 mmol) in DMSO (20 mL) was added aq. MeSNa (wt. 20%, 40 mL, 116 mmol), followed by CuI (270 mg, 1.94 mmol). The mixture was degassed and refilled with nitrogen. The reaction was heated at 150 C. overnight. After cooled to RT, the volatiles were removed and the residue was purified by column (PE/EtOAc=2/1 to 1/1) to give 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (3.2 g, yield: 50%) as a yellow solid. MS obsd. (ESI+) [(M+H)+] 166.0. To a solution of 3-(methylthio)-1H-pyrazolo[3,4-c]pyridine (10 g, 60.6 mmol) in DMF (100 mL) was added oxone (37 g, 121.2 mmol.) in portions. The reaction mixture was stirred at RT. After the reaction completed, water (100 mL) was added. The reaction was quenched carefully by addition of Na2SO3 and Na2CO3. The solid was filtered off and washed with MeOH (300 mL). The filtrate was concentrated under vacuum and the residue was purified by chromatography on silica gel column (DCM/MeOH=20/1) to give 3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (10.7 g, yield: 90%) as a yellow solid. MS obsd. (ESI+) [(M+H)+] 198.0.
  • 8
  • [ 1082040-63-8 ]
  • [ 1538625-64-7 ]
  • 10
  • [ 1082040-63-8 ]
  • 4-(5-chloro-2-[3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl]methyl}-1H-benzimidazol-1-yl)pyrrolidin-2-one [ No CAS ]
  • 11
  • [ 1082040-63-8 ]
  • 1-({5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine [ No CAS ]
  • 13
  • [ 1082040-63-8 ]
  • 1-({5-chloro-7-fluoro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine [ No CAS ]
  • 15
  • [ 1082040-63-8 ]
  • [ 1528560-45-3 ]
  • 16
  • [ 1082040-63-8 ]
  • 1-[5-chloro-1-((R)-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-1H-benzoimidazol-2-ylmethyl]-3-methanesulfonyl-1H-pyrazolo[3,4-c]pyridine [ No CAS ]
 

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