[ CAS No. 7598-35-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 7598-35-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 7598-35-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7598-35-8 ]

SDS Specification

Alternatived Products of [ 7598-35-8 ]

Product Details of [ 7598-35-8 ]

CAS No. :	7598-35-8	MDL No. :	MFCD01646061
Formula :	C₅H₅BrN₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	GNTGEMWEXKBWBX-UHFFFAOYSA-N
M.W :	173.01	Pubchem ID :	346455
Synonyms :

Calculated chemistry of [ 7598-35-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.34
TPSA :	38.91 ?2

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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.27
Log Po/w (XLOGP3) :	1.2
Log Po/w (WLOGP) :	1.43
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	1.41
Consensus Log Po/w :	1.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	1.03 mg/ml ; 0.00597 mol/l
Class :	Soluble
Log S (Ali) :	-1.61
Solubility :	4.21 mg/ml ; 0.0243 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.51
Solubility :	0.531 mg/ml ; 0.00307 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 7598-35-8 ]

Signal Word:	Danger	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H318-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7598-35-8 ]

* 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.

Upstream synthesis route of [ 7598-35-8 ]
Downstream synthetic route of [ 7598-35-8 ]

[ 7598-35-8 ] Synthesis Path-Upstream 1~2

1
[ 7598-35-8 ]
[ 98-80-6 ]
[ 21203-86-1 ]

Yield	Reaction Conditions	Operation in experiment
100 %Spectr.	With palladium diacetate In water at 100℃; for 1 h; Inert atmosphere	[0032] A mixture of 4-amino-2-bromopyridine (1.730 g, 10 mmol, 1.0 equiv), (0045) phenylboronic acid (1.341 g, 11 mmol, 1.1 equiv), Pd(OAc)₂ ((0.0449 g, 0.2 mmol, 0.02 equiv) or (0.0898 g, 0.4 mmol, 0.04 equiv) as identified in Table 1) and H₂0 (25 mL, 1384 mmol) in a 3 -neck round-bottom flask was well stirred under reflux at 100 °C in a N₂ atmosphere for the time listed in Table 1. The initial and final pH values of the aqueous phase were measured before and after the heating was enabled when the temperature was stabilized at 25 - 27 °C, and listed in Table 1. The initial reaction time (t = 0) was taken when the reaction mixture reached an internal temperature of 100 °C; the time to reach this temperature was approximately 20 - 30 minutes. The reactions were biphasic with an aqueous phase and a solid phase. The cooled reaction mixture was basified to pH > 12 using 30percent NaOH aqueous solution, and then thoroughly extracted with ethyl acetate. The combined organic phase was dried over anhydrous MgSC _, filtered, and then concentrated in vacuo. The crude product was analyzed by GC and ^{FontWeight="Bold" FontSize="10"}Η NMR, as provided in Table 1.

Reference： [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 38, p. 7598 - 7602
[2] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1489 - 1499
[3] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8520 - 8529
[4] Patent: WO2017/112576, 2017, A1, . Location in patent: Paragraph 0032
[5] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432

2
[ 7598-35-8 ]
[ 21203-86-1 ]

Yield	Reaction Conditions	Operation in experiment
100 %Chromat.	With palladium diacetate In water at 100℃; for 4 h; Inert atmosphere	[0043] A mixture of 4-amino-2-bromopyridine (1.730 g, 10 mmol, 1.0 equiv), potassium phenyltrifluoroborate (2.760 g, 15 mmol, 1.5 equiv), Pd(OAc)₂ (0.0898 g, 0.4 mmol, 0.04 equiv) and 0 (25 mL, 1384 mmol) in a 3-neck round-bottom flask was well stirred under reflux at 100 °C in a N₂ atmosphere for 4 h. The initial and final pH values of the aqueous phase were measured before and after the heating was enabled when the temperature was stabilized at 25 - 27 °C. The initial reaction time (t = 0) was taken when the reaction mixture reached an internal temperature of 100 °C; the time to reach this temperature was approximately 20 - 30 minutes. The reaction was biphasic with an aqueous phase and a solid phase. The cooled reaction mixture was basified to pH > 12 using 30percent NaOH aqueous solution, and then thoroughly extracted with ethyl acetate. The combined organic phase was dried over anhydrous MgS0_4, filtered, and then concentrated in vacuo. The crude product was analyzed by GC, as provided in Table 6.

Reference： [1] Patent: WO2017/112576, 2017, A1, . Location in patent: Paragraph 0042-0043

[ 7598-35-8 ] Synthesis Path-Downstream 1~3

1
[ 7598-35-8 ]
[ 151-50-8 ]
[ 10386-27-3 ]

Reference： [1]Roczniki Chemii,1957,vol. 31,p. 569,574
Chem.Abstr.,1958,p. 5407

2
[ 7598-35-8 ]
[ 98-80-6 ]
[ 21203-86-1 ]

Yield	Reaction Conditions	Operation in experiment
61.8%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 110℃;Sealed tube;	2-Bromopyridin-4-amine (150 mg, 0.86 mmol), 11 phenylboronic acid (211.4 mg, 1.73 mmol) and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (42.46 mg, 0.054 mmol) were suspended in a mixture of 12 Cs2CO3 2M in 13 water (1.3 mL, 2.60 mmol) and 6.5 mL of 14 1,4-Dioxane. The reaction mixture was degassed and the vial was sealed and heated at 110C overnight. The reaction was quenched with 15 NaOH 1 M and extracted two times with ethyl acetate. The organic layer was washed (NaHCO3 saturated and Brine), dried with sodium sulphate and concentrated under vacuum. The crude was purified by CombiFlash column chromatography (Cyclohexane: Ethyl Acetate) to obtain the 16 amine derivative (91.2 mg, 61.8%). 1H-NMR (400 MHz, DMSO-d6): delta = 8.08 (d, 1 H), 7.90 (d, 2H), 7.44 (t, 2H), 7.37 (t, 1 H), 6.99 (d, 1 H), 6.45 (dd, 1 H), 6.07 (s, 2H). HPLC-MS: Rt 3.014; m/z 170.9 (MH+).
100%Spectr.	With palladium diacetate; In water; at 100℃; for 1.0h;Inert atmosphere;	[0032] A mixture of 4-amino-2-bromopyridine (1.730 g, 10 mmol, 1.0 equiv), (0045) phenylboronic acid (1.341 g, 11 mmol, 1.1 equiv), Pd(OAc)2 ((0.0449 g, 0.2 mmol, 0.02 equiv) or (0.0898 g, 0.4 mmol, 0.04 equiv) as identified in Table 1) and H20 (25 mL, 1384 mmol) in a 3 -neck round-bottom flask was well stirred under reflux at 100 C in a N2 atmosphere for the time listed in Table 1. The initial and final pH values of the aqueous phase were measured before and after the heating was enabled when the temperature was stabilized at 25 - 27 C, and listed in Table 1. The initial reaction time (t = 0) was taken when the reaction mixture reached an internal temperature of 100 C; the time to reach this temperature was approximately 20 - 30 minutes. The reactions were biphasic with an aqueous phase and a solid phase. The cooled reaction mixture was basified to pH > 12 using 30% NaOH aqueous solution, and then thoroughly extracted with ethyl acetate. The combined organic phase was dried over anhydrous MgSC , filtered, and then concentrated in vacuo. The crude product was analyzed by GC and FontWeight="Bold" FontSize="10" Eta NMR, as provided in Table 1.

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 7598 - 7602
[2]Patent: EP3498694,2019,A1 .Location in patent: Paragraph 0097-0098
[3]Journal of Medicinal Chemistry,2019
[4]Organic Process Research and Development,2016,vol. 20,p. 1489 - 1499
[5]Journal of Organic Chemistry,2016,vol. 81,p. 8520 - 8529
[6]Patent: WO2017/112576,2017,A1 .Location in patent: Paragraph 0032
[7]New Journal of Chemistry,2017,vol. 41,p. 15420 - 15432

3
[ 7598-35-8 ]
potassium phenyltrifluoborate [ No CAS ]
[ 21203-86-1 ]

Yield	Reaction Conditions	Operation in experiment
100%Chromat.	With palladium diacetate; In water; at 100℃; for 4.0h;Inert atmosphere;	[0043] A mixture of 4-amino-2-bromopyridine (1.730 g, 10 mmol, 1.0 equiv), potassium phenyltrifluoroborate (2.760 g, 15 mmol, 1.5 equiv), Pd(OAc)2 (0.0898 g, 0.4 mmol, 0.04 equiv) and 0 (25 mL, 1384 mmol) in a 3-neck round-bottom flask was well stirred under reflux at 100 C in a N2 atmosphere for 4 h. The initial and final pH values of the aqueous phase were measured before and after the heating was enabled when the temperature was stabilized at 25 - 27 C. The initial reaction time (t = 0) was taken when the reaction mixture reached an internal temperature of 100 C; the time to reach this temperature was approximately 20 - 30 minutes. The reaction was biphasic with an aqueous phase and a solid phase. The cooled reaction mixture was basified to pH > 12 using 30% NaOH aqueous solution, and then thoroughly extracted with ethyl acetate. The combined organic phase was dried over anhydrous MgS04, filtered, and then concentrated in vacuo. The crude product was analyzed by GC, as provided in Table 6.

Reference： [1]Patent: WO2017/112576,2017,A1 .Location in patent: Paragraph 0042-0043

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

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[ 7598-35-8 ]

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[ 7598-35-8 ]

Pyridines

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[ CAS No. 7598-35-8 ] {[proInfo.proName]}

Quality Control of [ 7598-35-8 ]

Related Doc. of [ 7598-35-8 ]

Product Details of [ 7598-35-8 ]

Calculated chemistry of [ 7598-35-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7598-35-8 ]

Application In Synthesis of [ 7598-35-8 ]

[ 7598-35-8 ] Synthesis Path-Upstream 1~2

[ 7598-35-8 ] Synthesis Path-Downstream 1~3

Technical Information

Related Functional Groups of [ 7598-35-8 ]

Bromides

Amines

Related Parent Nucleus of [ 7598-35-8 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 7598-35-8 ]

Related Parent Nucleus of
[ 7598-35-8 ]