[ CAS No. 1357947-08-0 ] {[proInfo.proName]}

Name: 1357947-08-0|5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine|95%
Brand: Ambeed
SKU: A117844
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Quality Control of [ 1357947-08-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1357947-08-0 ]

SDS Specification

Alternatived Products of [ 1357947-08-0 ]

Product Details of [ 1357947-08-0 ]

CAS No. :	1357947-08-0	MDL No. :	MFCD21647868
Formula :	C₆H₃BrIN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NLQYLFQIAAPJFX-UHFFFAOYSA-N
M.W :	323.92	Pubchem ID :	71743113
Synonyms :

Calculated chemistry of [ 1357947-08-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.31
TPSA :	41.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	2.19
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	1.85
Log Po/w (SILICOS-IT) :	3.21
Consensus Log Po/w :	2.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.83
Solubility :	0.0475 mg/ml ; 0.000147 mol/l
Class :	Soluble
Log S (Ali) :	-2.7
Solubility :	0.651 mg/ml ; 0.00201 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.32
Solubility :	0.0156 mg/ml ; 0.0000482 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.39

Safety of [ 1357947-08-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1357947-08-0 ]

* 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.

Upstream synthesis route of [ 1357947-08-0 ]
Downstream synthetic route of [ 1357947-08-0 ]

[ 1357947-08-0 ] Synthesis Path-Upstream 1~3

1
[ 929617-35-6 ]
[ 1357947-08-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5258 - 5264
[2] Patent: WO2013/24002, 2013, A1, . Location in patent: Page/Page column 128

2
[ 23056-47-5 ]
[ 1357947-08-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5258 - 5264

3
[ 156118-16-0 ]
[ 1357947-08-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5258 - 5264

[ 1357947-08-0 ] Synthesis Path-Downstream 1~30

1
[ 1357947-08-0 ]
[ 1692-25-7 ]
[ 1422438-87-6 ]

Yield	Reaction Conditions	Operation in experiment
28%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 160℃; for 1.0h;Inert atmosphere; Microwave irradiation;	To a microwave tube was added 5-bromo-3-iodo-lH-pyrazolo[3,4-c]pyridine (100 mg, 0.31 mmol), pyridin-3-ylboronic acid (343 mg, 2.79 mmol), Pd(dppf)Cl2 (24 mg, 0.03 mmol), sodium carbonate (131 mg, 1.24 mmol), 1 ,2-dimethoxyethane (2 mL), ethanol (0.5 mL) and water (0.5 mL). The tube was flushed with nitrogen for 2 minutes and heated in a Biotage microwave at 160 C for 1 hour. The solvent was distilled off and the crude product was purified via reverse phase HPLC eluting with 15%> CH3CN in aqueous 10 mmol NH4HC03 to afford 176 as a pale yellow solid (30 mg, 28%). 1H NMR (500 MHz, DMSO) 1H NMR (500 MHz, DMSO) delta 14.1 (s, 1H), 9.44 (s, 1H), 9.37 (s, 3H), 9.26 (s, 1H), 8.71 (s, 1H), 8.67 - 8.66 (m, 1H), 8.60 - 8.59 (m, 2H), 8.56 -8.54 (m, 1H), 7.60 - 7.58 (m, 1H), 7.52 - 7.51 (m, 1H). ESI MS m/z = 274 (M+l)

Reference： [1]Patent: WO2013/24002,2013,A1 .Location in patent: Page/Page column 150-151

2
[ 929617-35-6 ]
[ 1357947-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃;	A solution containing 5-bromo-lH-pyrazolo[3,4-c]pyridine (168.0 g, 848.4 mmol) and NIS (286.3 g, 1.27 mol) in DMF (1.2 L) was stirred on at room temperature. The reaction mixture was poured into water then filtered. The solid was washed with water and 5% Na2S205. The crude product was dried under high vacuum overnight to give 5-bromo-3-iodo-lH- pyrazolo[3,4-c]pyridine.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264
[2]Patent: WO2013/24002,2013,A1 .Location in patent: Page/Page column 128

3
[ 23056-47-5 ]
[ 1357947-08-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

4
[ 156118-16-0 ]
[ 1357947-08-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

5
[ 110-87-2 ]
[ 1357947-08-0 ]
[ 1369509-72-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

6
[ 1357947-08-0 ]
[ 1422440-68-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

7
[ 1357947-08-0 ]
[ 1422442-84-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

8
[ 1357947-08-0 ]
C₂₁H₂₁FN₆O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

9
[ 1357947-08-0 ]
C₃₀H₃₈N₈O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5258 - 5264

10
[ 5292-43-3 ]
[ 1357947-08-0 ]
tert-butyl 2-(5-bromo-3-iodo-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;Reflux; Inert atmosphere;	To a solution of <strong>[1357947-08-0]5-bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine</strong> (1 equiv) in CH3CN (10 vol) was added tert-butyl 2-bromoacetate (1.1 equiv) and potassium carbonate (1.1 equiv). The mixturewas refluxed overnight under an atmosphere of argon. After cooling the reaction mixture to room temperature, the mixture was filtered through Celite and washed with CH3CN. The filtrate was concentrated under reduced pressure and the remaining residue was purified by column chromatography on silica gel (eluted with DCMIMeOH) to afford compound 104-S2.

Reference： [1]Patent: WO2018/160889,2018,A1 .Location in patent: Page/Page column 539; 540

11
[ 1357947-08-0 ]
(1R,3S,5R)-2-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-pyrazolo[3,4-c]pyridin-1-yl)acetyl)-N-(6-bromo-3-methylpyridin-2-yl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxamide [ No CAS ]