[ CAS No. 1146615-52-2 ] {[proInfo.proName]}

Name: 1146615-52-2|3-Bromo-6-iodo-imidazo[1,2-a]pyridine|97%
Brand: Ambeed
SKU: A501698
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Quality Control of [ 1146615-52-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1146615-52-2 ]

Product Details of [ 1146615-52-2 ]

CAS No. :	1146615-52-2	MDL No. :	MFCD14584657
Formula :	C₇H₄BrIN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LZAXVCBLZXZVCK-UHFFFAOYSA-N
M.W :	322.93	Pubchem ID :	68484830
Synonyms :

Calculated chemistry of [ 1146615-52-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.61
TPSA :	17.3 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) :	-5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	3.44
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	2.35
Log Po/w (SILICOS-IT) :	2.59
Consensus Log Po/w :	2.67

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.61
Solubility :	0.00784 mg/ml ; 0.0000243 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.48
Solubility :	0.106 mg/ml ; 0.000328 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.0441 mg/ml ; 0.000136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.4

Safety of [ 1146615-52-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1146615-52-2 ]

* 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 [ 1146615-52-2 ]

[ 1146615-52-2 ] Synthesis Path-Downstream 1~22

1
[ 1146615-52-2 ]
[ 27489-62-9 ]
4-(3-bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide In ethylene glycol; isopropyl alcohol at 80℃; for 40h;	2.1.1 Step 1: 4-(3-Bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol Copper (I) iodide (0.1 eq, 1.45 g, 7.68 mmol) and potassium phosphate tribasic (2 eq, 0.153 mol, 32.5 g) are stirred at RT under an atmosphere of argon during the addition of 3-bromo-6-iodo-imidazo[1,2-a]pyridine (Intermediate F) ( 25 g, 77 mmol, 1 eq) in isopropyl alcohol (200 ml), ethylene glycol (2 eq, 0.153 mol, 8.5 ml) and finally trans- 4-aminocyclohexanol (2 eq, 17.5 g, 153 mmol) The reaction is heated at 80 °C for 40 hours. The majority of the solvent is removed in vacuo and the residue is diluted with water (500 ml) and extracted with EtOAc (3 x 500 ml). The combined organic portions are dried (MgSθ4) and concentrated in vacuo. Purification by flash chromatography on silica eluting with 0-15 % MeOH in EtOAc gives 4-(3-bromo- imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol; [M+H]+ = 310 (312)

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2009/50183, 2009, A2 Location in patent: Page/Page column 100

2
[ 1146615-52-2 ]
[ 721884-81-7 ]
[ 1146615-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-bromo-6-iodoimidazo[1,2-a]pyridine With potassium phosphate; ethylene glycol In isopropyl alcohol at 20℃; Stage #2: (1S,3S)-3-aminocyclohexanol With copper(l) iodide In isopropyl alcohol at 85℃; for 40h;	U1 3-Bromo-6-iodo-imidazo[1,2-a]pyridine (Intermediate F) (1.5 eq, 59.0 mmol, 19 g), ethylene glycol (2 eq, 79 mmol, 4.39 ml) and potassium phosphate tribasic (2 eq, 79 mmol, 16.7 g) in isopropyl alcohol (262 ml) are stirred at RT under an atmosphere of argon during. Trans-(S/S)-3-aminocyclohexanol (1.0 eq, 39 mmol, 4.5 g) is added followed by copper (I) iodide (0.1 eq, 3.93 mmol, 0.8 g). The reaction is heated at 85 °C for 40 hours. The majority of the solvent is removed in vacuo and the residue is diluted with water (500 ml) and EtOAc (500 ml). The biphasic mixture is passed through a pad of CeIi te 521. The combined organic portions are washed with brine, dried (MgSθ4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 50-100% EtOAc in iso-hexane to afford the title compound; [M+H]+ = 310 (312).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2009/50183, 2009, A2 Location in patent: Page/Page column 125

3
[ 426825-75-4 ]
[ 1146615-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In acetic acid at 20℃; for 1h;	F2 To a mixture comprising 6-iodo-imidazo[1,2-a]pyridine (1 eq, 95 mmol, 23.3 g) in acetic acid (220 ml) under an inert atmosphere of argon is added dropwise bromine (1 eq, 95 mmol, 4.8 ml). After stirring at room temperature for 1 hour, the reaction mixture is filtered. The resulting solid is suspended in DCM (1% MeOH) (500 ml) and washed with 4N sodium hydroxide (100 ml). When the solid dissolves, the organic layer is separated, dried (MgSO4) and evaporated to give a beige solid; [M+H]+ 323 (325).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2009/50183, 2009, A2 Location in patent: Page/Page column 118

4
[ 1146615-52-2 ]
(+/-)-trans-3-aminocyclohexanol [ No CAS ]
(1RS,3RS)-3-(3-bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; ethylene glycol In isopropyl alcohol at 95℃; for 40h;	J1 Copper (I) iodide (0.1 eq, 0.8 g, 0.43 mmol) and potassium phosphate tribasic (2 eq, 43.4 mmol, 9.2 g) are stirred at RT under an atmosphere of argon during the addition of 3-bromo-6-iodo-imidazo[1,2-a]pyridine (Intermediate F) ( 7 g, 21.7 mmol, 1 eq) in isopropyl alcohol (75 ml), ethylene glycol (2 eq, 43.4 mmol, 2.4 ml) and finally trans- (RS/RS)-3-aminocyclohexanol (2 eq, 5 g, 43.4 mmol). The reaction is heated at 95 °C for 40 hours. The majority of the solvent is removed in vacuo and the residue is diluted with water (500 ml) and extracted with (9:1) EtOAc: Methanol (3 x 500 ml). The combined organic portions are passed through SCX (solid-supported sulfonic acid) resin (95g) eluting with MeOH followed by 2M NH3 in MeOH (250 ml). The basic ammonia wash is concentrated in vacuo and purification of the residue by flash chromatography on silica eluting with EtOAc affords the title compound; [M+H]+ = 310 (312).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2009/50183, 2009, A2 Location in patent: Page/Page column 120

5
[ 1146615-52-2 ]
3-(4-cyclopropylphenyl)-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 0.25 h / 90 °C / Inert atmosphere; Microwave irradiation 2: [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; potassium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 0.25 h / 100 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 15 h / 90 °C / Microwave irradiation 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / lithium hydroxide monohydrate; tetrahydrofuran / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: ARISAN THERAPEUTICS - WO2018/13430, 2018, A2
[2]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1

6
[ 1146615-52-2 ]
3-(4-cyclopropoxyphenyl)-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 0.25 h / 90 °C / Inert atmosphere; Microwave irradiation 2: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / lithium hydroxide monohydrate; tetrahydrofuran / 0.25 h / 100 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 5 h / 90 °C / Inert atmosphere 2: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 15 h / 90 °C / Microwave irradiation 2: tetrakis-(triphenylphosphine)-palladium; potassium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: ARISAN THERAPEUTICS - WO2018/13430, 2018, A2
[2]Plewe, Michael B.; Gantla, Vidyasagar Reddy; Sokolova, Nadezda V.; Shin, Young-Jun; Naik, Shibani; Brown, Eric R.; Fetsko, Alexandra; Zhang, Lihong; Kalveram, Birte; Freiberg, Alexander N.; Henkel, Greg; McCormack, Ken [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]
[3]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1

7
[ 1146615-52-2 ]
3-[4-(difluoromethoxy)phenyl]-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / lithium hydroxide monohydrate; 1,4-dioxane / 0.25 h / 90 °C / Inert atmosphere; Microwave irradiation 2: Palladium⁽⁰⁾ bis(dibenzylideneacetone); tricyclohexylphosphine; potassium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 0.25 h / 100 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 15 h / 90 °C / Microwave irradiation 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / lithium hydroxide monohydrate; tetrahydrofuran / 100 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: ARISAN THERAPEUTICS - WO2018/13430, 2018, A2
[2]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1

8
[ 1146615-52-2 ]
3-(4-{1-[(tert-butyldimethylsilyl)oxy]cyclopropyl}phenyl)-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 0.25 h / 90 °C / Inert atmosphere; Microwave irradiation 2: [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; potassium carbonate / water; tetrahydrofuran / 0.25 h / 100 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: ARISAN THERAPEUTICS - WO2018/13430, 2018, A2

9
[ 1146615-52-2 ]
[ 153624-46-5 ]
3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 15h; Microwave irradiation;	C30.1 Step 1: 3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine 3-bromo-6-iodoimidazo[1,2-a]pyridine (100 mg, 0.3 mmol) was added to a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodium carbonate (94 mg, 0.9 mmol), 3 mL of 1,4-dioxane, and 1 mL of water. The mixture was capped tightly and degassed by bubbling nitrogen through the septum for 5 minutes. The resulting solution was heated to 90oC for 15 minutes in a microwave reactor and allowed to cool. The mixture was then diluted with ethyl acetate, washed with water (2x) and brine (1x), dried over sodium sulfate, and evaporated. The crude oil was purified by flash chromatography on silica (1:1 hexanes:ethyl acetate, isocratic) to provide the title compound (82 mg) as a light yellow oil that slowly solidified. LC/MS m/z: 331.24 (79Br, M+H)+, 333.28(81Br, M+H)+.
83%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 15h; Microwave irradiation;	C30.1 Step 1: 3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine 3-bromo-6-iodoimidazo[1,2-a]pyridine (100 mg, 0.3 mmol) was added to a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodium carbonate (94 mg, 0.9 mmol), 3 mL of 1,4-dioxane, and 1 mL of water. The mixture was capped tightly and degassed by bubbling nitrogen through the septum for 5 minutes. The resulting solution was heated to 90oC for 15 minutes in a microwave reactor and allowed to cool. The mixture was then diluted with ethyl acetate, washed with water (2x) and brine (1x), dried over sodium sulfate, and evaporated. The crude oil was purified by flash chromatography on silica (1:1 hexanes:ethyl acetate, isocratic) to provide the title compound (82 mg) as a light yellow oil that slowly solidified. LC/MS m/z: 331.24 (79Br, M+H)+, 333.28(81Br, M+H)+.
80%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 5h; Inert atmosphere;	3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine (2b) 3-bromo-6-iodoimidazo[1,2-a]pyridine (100 mg, 0.3 mmol) was addedto a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg,0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodiumcarbonate (94 mg, 0.9 mmol), 3 mL of 1,4-dioxane, and 1 mL of water. Themixture was capped tightly and degassed by bubbling nitrogen through the septumfor 5 minutes. The resulting solution was heated to 90 oC for 15minutes in a microwave reactor and allowed to cool. The mixture was thendiluted with ethyl acetate, washed with water (2x) and brine (1x), dried oversodium sulfate, and evaporated. The crude oil was purified by flash chromatographyon silica (1:1 hexanes:ethyl acetate, isocratic) to provide 82 mg (80%) of thetitle compound as a light yellow oil that slowly solidified. LC/MS m/z: calculated for C16H15BrN2O[79Br, M+H]+ 331.04, found 331.24; calculated for C16H15BrN2O[81Br, M+H]+ 333.04, found 333.28.

82 mg

With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 0.25h; Inert atmosphere; Microwave irradiation;

C30.1 Step 1: 3-bromo-6-[4-(propan-2-yloxy) phenyl]imidazo[1 ,2-a]pyridine 3-bromo-6-iodoimidazo[1 ,2-a]pyridine (100 mg, 0.3 mmol) was added to a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodium carbonate (94 mg, 0.9 mmol), 3 mL of 1 ,4-dioxane, and 1 mL of water. The mixture was capped tightly and degassed by bubbling nitrogen through the septum for 5 minutes. The resulting solution was heated to 90 °C for 15 minutes in a microwave reactor andallowed to cool. The mixture was then diluted with ethyl acetate, washed with water (2x) and brine(lx), dried over sodium sulfate, and evaporated. The crude oil was purified by flash chromatography on silica (1:1 hexanes:ethyl acetate, isocratic) to provide the title compound (82 mg) as a light yellow oil that slowly solidified. LCMS m/z: 331.24 (79Br, M+H), 333.28(81Br, M+H).

Reference： [1]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1 Location in patent: Page/Page column 76
[2]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1 Location in patent: Page/Page column 76
[3]Plewe, Michael B.; Gantla, Vidyasagar Reddy; Sokolova, Nadezda V.; Shin, Young-Jun; Naik, Shibani; Brown, Eric R.; Fetsko, Alexandra; Zhang, Lihong; Kalveram, Birte; Freiberg, Alexander N.; Henkel, Greg; McCormack, Ken [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]
[4]Current Patent Assignee: ARISAN THERAPEUTICS - WO2018/13430, 2018, A2 Location in patent: Page/Page column 100; 101

10
[ 1146615-52-2 ]
2-(((4,4-dimethylpentan-2-ylidene)amino)oxy)-2-methylpropanoic acid [ No CAS ]
methyl (E)-2-(((5-(3-bromoimidazo[1,2-a]pyridin-6-yl)-4,4-dimethylpentan-2-ylidene)amino)oxy)-2-methylpropanoate [ No CAS ]
methyl (Z)-2-(((5-(3-bromoimidazo[1,2-a]pyridin-6-yl)-4,4-dimethylpentan-2-ylidene)amino)oxy)-2-methylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 5-nitro-2-pyridone; palladium diacetate; silver trifluoroacetate / 20 h / 120 °C 2: thionyl chloride / 0.5 h / 20 °C

Reference： [1]Zhu, Ru-Yi; Li, Zi-Qi; Park, Han Seul; Senanayake, Chris H.; Yu, Jin-Quan [Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3564 - 3568]

11
[ 1146615-52-2 ]
2-(((4,4-dimethylpentan-2-ylidene)amino)oxy)-2-methylpropanoic acid [ No CAS ]
C₁₈H₂₄BrN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 5-nitro-2-pyridone; palladium diacetate; silver trifluoroacetate at 120℃; for 20h;

Reference： [1]Zhu, Ru-Yi; Li, Zi-Qi; Park, Han Seul; Senanayake, Chris H.; Yu, Jin-Quan [Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3564 - 3568]

12
[ 1146615-52-2 ]
[ 108-91-8 ]
C₁₃H₁₆BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1,1,3',3',3'-hexafluoro-propanol; 2-chloro-6-hydroxybenzaldehyde; water; palladium diacetate; silver trifluoroacetate; 2-hydroxy-5-(trifluoromethyl)pyridine at 150℃; for 12h; Sealed tube;

Reference： [1]Chen, Yan-Qiao; Wang, Zhen; Wu, Yongwei; Wisniewski, Steven R.; Qiao, Jennifer X.; Ewing, William R.; Eastgate, Martin D.; Yu, Jin-Quan [Journal of the American Chemical Society, 2018, vol. 140, # 51, p. 17884 - 17894]

13
[ 1146615-52-2 ]
[ 108-91-8 ]
tert-butyl (3-(3-bromoimidazo[1,2-a]pyridin-6-yl)cyclohexyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: palladium diacetate; 2-chloro-6-hydroxybenzaldehyde; 2-hydroxy-5-(trifluoromethyl)pyridine; 1,1,1,3',3',3'-hexafluoro-propanol; silver trifluoroacetate; water / 12 h / 150 °C / Sealed tube 2.1: hydrogenchloride / tetrahydrofuran / 1 h / 20 °C 2.2: 4 h / 20 °C

14
[ 893440-50-1 ]
[ 1146615-52-2 ]
[ 1414472-94-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water at 110℃; for 0.666667h; Microwave irradiation;	5-(3-Bromo-imidazo[1,2-a]pyridin-6-yl)-2-methoxy-pyridin-3-ylamine (10e). From 3-Bromo-6-iodo-imidazo[1,2-a]pyridine 5 (0.5 g, 1.55 mmol), (5-amino-6-methoxypyridin-3-yl)boronic acid pinacol ester (426 mg, 1.705 mmol), Na2CO3 (657 mg, 6.2 mmol), Pd(dppf)Cl2 (43 mg, 0.0775 mmol), H2O (3 mL) and DME (6 mL), heating at 110 °C for 40 min under microwave irradiation and purification by column chromatography on silica gel using gradient 10% to 100% of EtOAc in cHex, 10e was obtained (280 mg, 57%).

Reference： [1]Álvarez, Rosa M.; García, Ana Belén; Riesco-Fagundo, Concepción; Martín, José I.; Varela, Carmen; Rodríguez Hergueta, Antonio; González Cantalapiedra, Esther; Oyarzabal, Julen; Di Geronimo, Bruno; Lorenzo, Milagros; Albarrán, M Isabel; Cebriá, Antonio; Cebrián, David; Martínez-González, Sonia; Blanco-Aparicio, Carmen; Pastor, Joaquín [European Journal of Medicinal Chemistry, 2021, vol. 211]

15
[ 1146615-52-2 ]
[ 1414472-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 0.67 h / 110 °C / Microwave irradiation 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.67 h / 150 °C / Microwave irradiation

16
[ 1146615-52-2 ]
[ 1414473-08-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 0.67 h / 110 °C / Microwave irradiation 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.67 h / 150 °C / Microwave irradiation

17
[ 1146615-52-2 ]
3-[3-(propan-2-yloxy)phenyl]-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 5 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Plewe, Michael B.; Gantla, Vidyasagar Reddy; Sokolova, Nadezda V.; Shin, Young-Jun; Naik, Shibani; Brown, Eric R.; Fetsko, Alexandra; Zhang, Lihong; Kalveram, Birte; Freiberg, Alexander N.; Henkel, Greg; McCormack, Ken [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]

18
[ 1146615-52-2 ]
3-[4-(tert-butoxy)phenyl]-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 5 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube

19
[ 1146615-52-2 ]
2-(4-{6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridin-3-yl}phenyl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 5 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube

20
[ 1146615-52-2 ]
1-(4-{6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridin-3-yl}phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 5 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube

21
[ 1146615-52-2 ]
2-(propan-2-yloxy)-5-{6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridin-3-yl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 5 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube

22
[ 1146615-52-2 ]
5-{6-[4-(propan-2yloxy)phenyl]imidazo[1,2-a]pyridin-3-yl}-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 5 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.25 h / 90 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 1146615-52-2 ]

Bromides

[ 1260759-52-1 ]

2-Bromo-6-iodoimidazo[1,2-a]pyridine

Similarity: 0.98

[ 4926-47-0 ]

3-Bromoimidazo[1,2-a]pyridine

Similarity: 0.82

[ 1221791-77-0 ]

3-Bromo-6-chloro-8-iodoimidazo[1,2-a]pyridine

Similarity: 0.82

[ 1260759-52-1 ]

2-Bromo-6-iodoimidazo[1,2-a]pyridine

Similarity: 0.98

[ 4926-47-0 ]

3-Bromoimidazo[1,2-a]pyridine

Similarity: 0.82

Iodides

[ 1260759-52-1 ]

2-Bromo-6-iodoimidazo[1,2-a]pyridine

Similarity: 0.98

[ 1221791-77-0 ]

3-Bromo-6-chloro-8-iodoimidazo[1,2-a]pyridine

Similarity: 0.82

[ 1260759-52-1 ]

2-Bromo-6-iodoimidazo[1,2-a]pyridine

Similarity: 0.98

[ 1221791-77-0 ]

3-Bromo-6-chloro-8-iodoimidazo[1,2-a]pyridine

Similarity: 0.82

Related Parent Nucleus of
[ 1146615-52-2 ]

Other Aromatic Heterocycles

[ 1260759-52-1 ]

2-Bromo-6-iodoimidazo[1,2-a]pyridine

Similarity: 0.98

[ 4926-47-0 ]

3-Bromoimidazo[1,2-a]pyridine

Similarity: 0.82

[ 1221791-77-0 ]

3-Bromo-6-chloro-8-iodoimidazo[1,2-a]pyridine

Similarity: 0.82

[ 1260759-52-1 ]

2-Bromo-6-iodoimidazo[1,2-a]pyridine

Similarity: 0.98

[ 4926-47-0 ]

3-Bromoimidazo[1,2-a]pyridine

Similarity: 0.82

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1146615-52-2 ] {[proInfo.proName]}

Quality Control of [ 1146615-52-2 ]

Related Doc. of [ 1146615-52-2 ]

Product Details of [ 1146615-52-2 ]

Calculated chemistry of [ 1146615-52-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1146615-52-2 ]

Application In Synthesis of [ 1146615-52-2 ]

[ 1146615-52-2 ] Synthesis Path-Downstream 1~22

Related Functional Groups of [ 1146615-52-2 ]

Bromides

Iodides

Related Parent Nucleus of [ 1146615-52-2 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1146615-52-2 ]

Related Parent Nucleus of
[ 1146615-52-2 ]