[ CAS No. 913373-43-0 ] {[proInfo.proName]}

Name: 913373-43-0|2-Chloro-5-fluoropyridine-3-boronic acid|97%
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SKU: A705446
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Quality Control of [ 913373-43-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 913373-43-0 ]

Product Details of [ 913373-43-0 ]

CAS No. :	913373-43-0	MDL No. :	MFCD03094988
Formula :	C₅H₄BClFNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DRMCJBKKTDFORC-UHFFFAOYSA-N
M.W :	175.35	Pubchem ID :	24901774
Synonyms :

Safety of [ 913373-43-0 ]

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 [ 913373-43-0 ]

* 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.

Downstream synthetic route of [ 913373-43-0 ]

[ 913373-43-0 ] Synthesis Path-Downstream 1~4

1
[ 913373-43-0 ]
[ 52522-99-3 ]
[ 952402-70-9 ]

Yield	Reaction Conditions	Operation in experiment
27%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 4h;Heating / reflux;	Preparation 70: 5-(2-Chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep70); <n="100"/>5-lodo-2,4-dimethoxy-pyrimidine (868 mg, 3.3 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-chloro-5-fluoropyridine-3-boronic acid (858 mg, 4.9 mmol), Na2CO3 (700 mg, 6.6 mmol), PPh3 (88 mg, 0.33 mmol) and Pd(OAc)2 (90 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between brine and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether 2-8 affording 240 mg of the title compound (27% yield). MS (ES) (m/z): 270 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 97-98

2
[ 913373-43-0 ]
[ 943152-85-0 ]
[ 943153-01-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation;	(R)-N-{1-[4-(2-Chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethyl}-3,4-difluoro-benzenesulfonamide To a solution of (R)-2-[1-(4-bromo-phenyl)-ethyl]-isoindole-1,3-dione (1.19 g, 3.6 mmol) (Example 26) in 1,2-dimethoxyethane (3 ml) was added <strong>[913373-43-0]2-chloro-5-fluoropyridine-3-boronic acid</strong> (0.95 g, 5.4 mmol), tetrakis(triphenylphosphine)palladium (0) (0.21 g, 0.2 mmol) and 2M aqueous sodium carbonate (3.2 ml, 6.4 mmol). The reaction mixture was heated in a microwave oven at 150 C. for 10 min and the solvent evaporated. The residue was partitioned between ethyl acetate and water. The organic phase washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified over silica gel eluting with heptane/ethyl acetate to give (R)-2-{1-[4-(2-chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethyl}-isoindole-1,3-dione (0.62 g, 1.6 mmol, 44%) as a clear glass. To a solution of (R)-2-[1-(4-bromo-phenyl)-ethyl]-isoindole-1,3-dione (0.16 g, 0:4 mmol) in methanol (4 ml) was added hydrazine hydrate (0.43 g, 8.6 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. Dichloromethane was added and the resultant white precipitate filtered off. The solvent was evaporated to give 1-[4-(2-chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethylamine (0.11 g, 0.4 mmol, 100%) as a yellow gum. To a solution of (R)-1-[4-(2-chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethylamine (26 mg, 0.1 mmol) in dichloromethane (1 ml) was added triethylamine (31.6 mg, 0.31 mmol) followed by 3,4-difluorobenzenesulfonyl chloride (28.7 mg, 0.14 mmol). The reaction mixture was agitated for 64 h at room temperature and the solvent evaporated. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (6.7 mg, 0.04 mmol, 38%). 1H NMR (400 MHz, DMSO-d6): δ 8.48 (m, 2H), 7.78 (dd, 1H), 7.45-7.60 (m, 3H), 7.27-7.34 (m, 4H), 4.50 (q, 1H), 1.33 (d, 3H) ppm; MS (ESI) m/z: 427 [M+H]+.

Reference： [1]Patent: US2007/149577,2007,A1 .Location in patent: Page/Page column 11-12

3
[ 913373-43-0 ]
[ 1065481-12-0 ]
[ 1065481-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 100℃; for 1h;Microwave irradiation;	Example 80; <n="132"/>A mixture of (S)-2-(l-(2,8-dichloroquinolin-3-yl)ethyl)isoindoline-l,3-dione (120.0 mg, 323 μmol), <strong>[913373-43-0]2-chloro-5-fluoropyridin-3-ylboronic acid</strong> (57 mg, 323 μmol), tetrakis(triphenylphosphine)palladium (37 mg, 32 μmol), cesium fluoride (147 mg, 970 μmol) and copper(I) iodide (12 mg, 65 μmol) in 1 ,2-ethanediol, dimethyl ether (3.0 mL, 323 μmol) was subjected to microwave at 100 0C for 1 h, cooled to room temperature. Filtration of the resultant mixture and rinsed with EtOAc, the filtrates were collected and concentrated. Purification of the residue by flash chromatography over silica gel, gradient elution, 0-100% EtOAc in hexane, gave 2-((S)- 1 -(8-chloro-2-(2-chloro-5-fluoropyridin-3-yl)quinolin-3-yl)- ethyl)isoindoline-l,3-dione, Mass Spectrum (ESI) m/e = 466.0 (M + 1).

Reference： [1]Patent: WO2008/118468,2008,A1 .Location in patent: Page/Page column 130-131

4
[ 5419-55-6 ]
[ 884494-36-4 ]
[ 913373-43-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of n-BuLi/THF (1.45 mL, 2.5 mol/L) in THF (5 mL) was added asolution of <strong>[884494-36-4]3-bromo-2-chloro-5-fluoropyridine</strong> (630 mg, 3.0 mmol) in THF (5 mL) dropwise at-78 C. The reaction mixture was stirred at -78 C for another 30 minutes, followed by the addition of B(OiPr)3 (677 mg, 3.6 mmol) in THF (2 mL). The mixture was stirred at -78C for another 2 h, and quenched with 5% NaOH aqueous solution (10 mL). The mixture was acidified to pH 12 with dilute aqueous HC1 solution, and extracted with EA (60 mL x 3). Thecombined organic phases were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 2-chloro-5-fluoropyridin-3-ylboronic acid (1.5 g, crude) as grey oil, which was used in the next step without further purifications. LC-MS m/z: 176.1 [M+Hjt tR= 0.64 min.

Reference： [1]Patent: WO2017/176960,2017,A1 .Location in patent: Paragraph 00872

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P233	Keep container tightly closed.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
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H261	In contact with water releases flammable gas
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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. 913373-43-0 ] {[proInfo.proName]}

Quality Control of [ 913373-43-0 ]

Related Doc. of [ 913373-43-0 ]

Product Details of [ 913373-43-0 ]

Safety of [ 913373-43-0 ]

Application In Synthesis of [ 913373-43-0 ]

[ 913373-43-0 ] Synthesis Path-Downstream 1~4

Similar Product of [ 913373-43-0 ]

Related Functional Groups of [ 913373-43-0 ]

Fluorinated Building Blocks

Organoboron

Chlorides

Related Parent Nucleus of [ 913373-43-0 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 913373-43-0 ]

Related Functional Groups of
[ 913373-43-0 ]

Related Parent Nucleus of
[ 913373-43-0 ]