458532-98-4|(3-Chloropyridin-4-yl)boronic acid| Ambeed

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Quality Control of [ 458532-98-4 ] Purity: 96% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 458532-98-4 ]

CAS No. :	458532-98-4
Formula :	C₅H₅BClNO₂
M.W :	157.36
SMILES Code :	ClC1=C(B(O)O)C=CN=C1
MDL No. :	MFCD03425942
InChI Key :	JLIHQPWLAOYTRH-UHFFFAOYSA-N
Pubchem ID :	3861877

Safety of [ 458532-98-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 458532-98-4 ]

* 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 [ 458532-98-4 ]

[ 458532-98-4 ] Synthesis Path-Downstream 1~31

1
[ 626-60-8 ]
[ 458532-98-4 ]

References: [1]Tetrahedron,2002,vol. 58,p. 4369 - 4373.

2
[ 7745-93-9 ]
[ 458532-98-4 ]
[ 611225-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethylene glycol dimethyl ether; water; at 90℃; for 16.5h;	Step 1.Synthesis of 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine nitrogen was bubbled through a solution of 2-bromo-1-methyl-4-nitrobenzene (1 eq) in dimethoxyethane and water (3:1) for 0.5 h. bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by 3-chloro-4-pyridine boronic acid hydrate (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 90 C. for 16 h under nitrogen.The reaction mixture was concentrated and partitioned between ethyl acetate and water.The organic layer was washed with brine and dried with sodium sulfate and concentrated.Purification on silica gel gave 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine. MS: MH+=248.

References: [1]Patent: US2004/122237,2004,A1 .Location in patent: Page 201.

3
[ 1042370-06-8 ]
[ 458532-98-4 ]
1-[5-(4-chlorophenyl)-6-(3-chloro-pyridin-4-yl)-pyrazin-2-yl]-4-ethylamino-piperidine-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 130℃;	STEP 2. 1-[5-(4-CHLOROPHENYL)-O-(S-CHLORO-PYRIDIN^- YL)-PYRAZIN-2-YL]-4-ETHYLAMINO- PIPERIDINE-4-CARBOXYLIC ACBD AMIDEA mixture of l-[6-chloro-5-(4-chlorophenyl)-pyrazin-2-yl]-4-ethylamino-piperidine-4- carboxylic acid amide (26 mg, 0.065 mmol), 3-chloro-pyridine-4-yl boronic acid (31 mg, 0.2 mmol), Na2CO3 (43 mg, 0.41 mmol), Pd(PPh3)4 (8 mg), water (0.4 mL) and dioxane (1.0 mL) is degassed with argon for 10 min, then sealed and heated at 130ºC for overnight. The mixture is cooled, diluted with water (1 mL) and 1 N NaOH (0.5 mL), and extracted with EtOAc (2 mL). The extract is washed once with water and concentrated under vacuum. The residue is purified by PTLC (5% MeOH in CH2Cl2) to produce the title compound. LC-MS: m/z expected 471.4; found 472.2 (MH+), Rt=I .43 min.

References: [1]Patent: WO2006/113704,2006,A2 .Location in patent: Page/Page column 62.

4
[ 913282-76-5 ]
[ 458532-98-4 ]
4-[6-(3-chloro-pyridin-4-yl)-5-(4-trifluoromethyl-phenyl)-pyrazin-2-yloxy]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 135℃;	STEP 5. 4-[6-(3-CHLORO-PYRrom^-YL)-5-(4-TRIFLUOROMETHYL-PHENYL)-PYRAZIN-2-YLOXY]- PlPERIDlNE-l -CARBOXYLIC ACE) TERT-BVTYL ESTER4-[6-Chloro-5-(4-trifluoromethyl-phenyl)-pyrazin-2-yloxy]-piperidine-l -carboxylic acid tert- butyl ester (l.lg, 2.5 mmol), 3-chloro-pyridyl-4-boronic acid (1.3 g, 7.5 mmol) and Pd(PPh3)4 (64 mg,2 mol %) in 25 ml 1,4-dioxone is treated with 6.5 ml of 2M K2CO3 (12.5 mmol). The reaction mixture is heated to 135 ºC in a sealed tube overnight. After cooling, the reaction mixture is diluted with 100 ml EtOAc. The aqueous layer is extracted with EtOAc (2 X 20 ml). The combined organic layer is washed with sat. brine, dried over MgSO4, concentrated and purified by column chromatography to give the title compound. LC-MS: expected 534.96 (35Cl), found 535.3 (MH+).The Boc group may be replaced with a variety of moieties using, for example, the methods described in Examples 6 and 7.

References: [1]Patent: WO2006/113704,2006,A2 .Location in patent: Page/Page column 90.

5
[ 925677-89-0 ]
[ 458532-98-4 ]
5-(3-chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.166667h;	5-(3-Chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine A microwave oven reactor was charged with 5-bromo-6-(3-fluorophenyl)pyrazin-2-amine (Preparation 1 , 0.3 g, 1.11 mmol), <strong>[458532-98-4](3-chloropyridin-4-yl)boronic acid</strong> (212 mg, 1.03 mmol), [1 ,1'-bis(diphenylphosphino)ferrocene] palladium(ll)dichloride dichloromethane complex (1:1) (39 mg, 0.047 mmol), dioxane (8 ml_) and a 1.2M aqueous solution of cesium carbonate was added (1.9 ml_, 2.39 mmol). The mixture was heated to 15O0C for 10min in the microwave oven, then cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane to dichloromethane/methanol 90:10) furnished the title compound as a yellowish solid (78 mg, 39%). delta 1H-NMR (CDCI3): 8.55 (s, 1 H)1 8.45 (d, 1H), 8.05 (s, 1H), 7.30 (d, 1H), 7.15 (m,2H), 7.00 (m, 2H), 4.85 (bs, 2H).ESI/MS m/e: 301 ([M+H] C15H10CIFN4) Retention time (min.): 12

References: [1]Patent: WO2007/17096,2007,A1 .Location in patent: Page/Page column 106.

6
[ 1046460-72-3 ]
[ 458532-98-4 ]
C₂₄H₂₃ClF₂N₂O₂ [ No CAS ]
C₂₄H₂₃ClF₂N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3706 - 3710.

7
[ 1042370-06-8 ]
[ 458532-98-4 ]
1-[5-(4-chlorophenyl)-6-(3-chloropyridin-4-yl)pyrazin-2-yl]-4-(ethylamino)piperidine-4-carboxamide [ No CAS ]