5-Bromo-1H-pyrazolo[3,4-c]pyridine
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![5-Bromo-1H-pyrazolo[3,4-c]pyridine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220811/48ee89ff53624754a55d54a9a3a7601b.png "5-Bromo-1H-pyrazolo[3,4-c]pyridine")
5-Bromo-1H-pyrazolo[3,4-c]pyridine
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CAS No:
929617-35-6
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Formula:
C6H4BrN3
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Chemical Name:
5-Bromo-1H-pyrazolo[3,4-c]pyridine
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Synonyms:
1H-Pyrazolo[3,4-c]pyridine,5-bromo-;5-Bromo-1H-pyrazolo[3,4-c]pyridine
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CAS No:
Safety Information
22
Xn
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Bromo-1H-pyrazolo[3,4-c]pyridine Use and Manufacturing
To a solutionof 27(4.00 g, 21.4 mmol) in AcOH (300 ml) was added NaNOTo a stirred mixture of 5-bromo-l 7/-pyrazolo[3, 4 m-c]pyridine (5 g, 25.51 mmole) and DIEA (5.4 mL, 30.61 mmole) in DCM (50 mL) at 0C was added benzenesulfonyl chloride (3.6 mL, 28.06 mmole). After the addition was completed, the reaction mixture was stirred for 2h at RT. H20 was added, and the layers were separated. The organic layer was dried over Na2S04, concentrated to give the title compound (7.5 g, 87%). LC-MS (+ESI) M+H: 338.3.General procedure: To a stirred solution of 6-bromo-1 H-pyrrolo[3, 2-c]pyridine (1 g, 5.07 mmol) in DMF (25 mL), CS2CO3 (4.95 g, 15.21 mmol) and 4-(bromomethyl)pyridine hydrobromide (1 .92 g, 7.60 mmol) were added. The resulting suspension was allowed to stir at rt, and then heated to 50C for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc (2 x 120 mL). The organic layer was washed with water and brine solution, dried over anhydrous Na2S04, and filtered. The resulting solution was concentrated under reduced pressure to get a crude residue that was purified by flash column chromatography in 230-400 silica gel 70 % EtOAc/ pet ether as an eluent to afford the title compound (800 mg, 57.7 %) of the title compound as a light brown solid.General procedure: To a stirred solution of 6-bromo-1 H-pyrrolo[3, 2-c]pyridine (1 g, 5.07 mmol) in DMF (25 mL), CS2CO3 (4.95 g, 15.21 mmol) and 4-(bromomethyl)pyridine hydrobromide (1 .92 g, 7.60 mmol) were added. The resulting suspension was allowed to stir at rt, and then heated to 50C for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc (2 x 120 mL). The organic layer was washed with water and brine solution, dried over anhydrous Na2S04, and filtered. The resulting solution was concentrated under reduced pressure to get a crude residue that was purified by flash column chromatography in 230-400 silica gel 70 % EtOAc/ pet ether as an eluent to afford the title compound (800 mg, 57.7 %) of the title compound as a light brown solid.
Computed Properties
Molecular Weight:198.02
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-Bromo-1H-pyrazolo[3,4-c]pyridine
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