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Chemical Structure| 916325-84-3 Chemical Structure| 916325-84-3

Structure of 916325-84-3

Chemical Structure| 916325-84-3

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Product Details of [ 916325-84-3 ]

CAS No. :916325-84-3
Formula : C8H6BrN3O2
M.W : 256.06
SMILES Code : O=C(C1=NNC2=NC=C(Br)C=C21)OC
MDL No. :MFCD16661098
InChI Key :NWAGLGKQKQZPHF-UHFFFAOYSA-N
Pubchem ID :52911270

Safety of [ 916325-84-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 916325-84-3 ]

* 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 [ 916325-84-3 ]

[ 916325-84-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 916325-84-3 ]
  • [ 916325-85-4 ]
YieldReaction ConditionsOperation in experiment
100% Compound Ib (3.4 g, 13.2 mmol) in MeOH (50 mL) was refluxed with 2MNaOH (10 mL) for 4 hrs. The mixture was cooled to room temperature and acidified with hydrochloric acid to give Compound Ic (3.22 g, 100%). 1H NMR (300 MHz,CD3OD) delta 8.62 (s, IH), 8.58 (s, IH);' MS (ESI) m/z: 359 (M+H+).
92% Step 7[00181] A suspension of methyl 5-bromo-lH-pyrazolo[3,4-£]pyridine-3- carboxylate (VII) (70 mg, 0.27 mmol) in aqueous IN NaOH solution (20 mL) was heated at 90C for 3 h until the solution became clear. The solution was then cooled to 0C and acidified with a 10%> HC1 solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-lH-pyrazolo[3,4- £]pyridine-3-carboxylic acid (VIII) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCls) delta ppm 8.58 (d, J=3.01 Hz, 1 H), 8.66 (d, J=3.01 Hz, 1 H); ESIMS found for C7H4BrN302 mlz 242.1 (M+H).
92% spension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVII) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90 C. for 3 h until the solution became clear. The solution was then cooled to 0 C. and acidified with a 10% HCl solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVIII) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).
92% With water; sodium hydroxide; at 90℃; for 3h; Step 7 A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XV) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90 C. for 3 h until the solution became clear. The solution was then cooled to 0 C. and acidified with a 10% HCl solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVI) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).
92% With water; sodium hydroxide; at 0 - 90℃; for 3h; A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XV) (70 mg, 0.27 mmol) in aqueous IN NaOH solution (20 mL) was heated at 90C for 3 h until the solution became clear. The solution was then cooled to 0C and acidified with a 10% HC1 solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVI) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 8.58 (d, J=3.01Hz, 1H), 8.66 (d, J=3.01Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).

  • 2
  • [ 67-56-1 ]
  • [ 916325-85-4 ]
  • [ 916325-84-3 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; at 70℃; for 20h;Large scale; To a solution of <strong>[916325-85-4]5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid</strong> (XVIII) (1.6 Kg, 6.6 mol) in anhydrous MeOH (32 L) was added H2SO4 (160 mL). The reaction was slowly heated to 70 C. and stirred for 20 hours. The solution was concentrated under vacuum to a volume of 1.6 L. The residue was partitioned between DCM (120 L) and aqueous 10% NaHCO3 (32 L). The organic phase was separated and washed with aqueous 25% NaCl (32 L), dried over Na2SO4 and concentrated to a volume of 4.8 L. The product was crystallized by charging the solution with 3×n-heptane (8 L) while concentrating the volume to 4.8 L after each addition of n-heptane. The solid was filtered and dried under vacuum at 50 C. to produce methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVII) (1.53 Kg, 6.0 mol, 80.6% purity, 90.4% assay yield). 1H NMR (DMSO-d6, 400 MHz) delta ppm 3.95 (s, 3H), 8.62 (d, J=2 Hz, 1H), 8.73 (d, J=2.4 Hz, 1H), 14.78 (brs, 1H); ESIMS found C8H6BrN3O2 m/z 256.0 (M+H).
With sulfuric acid; at 70℃; for 2h;Large scale; To a solution of <strong>[916325-85-4]5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid</strong> (XXXIV) (1.6 Kg, 6.6 mol) in anhydrous MeOH (32 L) was added H2SO4 (160 mL). The reaction was slowly heated to 70oC and stirred for 20 hours. The solution was concentrated under vacuum to a volume of 1.6 L. The residue was partitioned between DCM (120 L) and aqueous 10% NaHCO3 (32 L). The organic phase was separated and washed with aqueous 25% NaCl (32 L), dried over Na2SO4 and concentrated to a volume of 4.8 L. The product was crystallized by charging the solution with 3 x n-heptane (8 L) while concentrating the volume to 4.8 L after each addition of n- heptane. The solid was filtered and dried under vacuum at 50oC to produce methyl 5-bromo-1H- pyrazolo[3,4-b]pyridine-3-carboxylate (XXXV) (1.53 Kg, 6.0 mol, 80.6% purity, 90.4% assay yield).1H NMR (DMSO-d6, 400 MHz) d ppm 3.95 (s, 3H), 8.62 (d, J=2Hz, 1H), 8.73 (d, J=2.4Hz, 1H), 14.78 (brs, 1H); ESIMS found C8H6BrN3O2 m/z 256.0 (M+H).
 

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