[ CAS No. 890839-31-3 ]

Name: 890839-31-3|2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid|96%
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Quality Control of [ 890839-31-3 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 890839-31-3 ]

Product Details of [ 890839-31-3 ]

CAS No. :	890839-31-3	MDL No. :	MFCD12546621
Formula :	C₁₃H₁₆BClO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	282.53 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 890839-31-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 890839-31-3 ]

Downstream synthetic route of [ 890839-31-3 ]

[ 890839-31-3 ] Synthesis Path-Downstream 1~7

1
[ 59748-90-2 ]
[ 73183-34-3 ]
[ 890839-31-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; dichloromethane; at 80℃; for 5h;	Preparation 11. 2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoic acid; To a solution of <strong>[59748-90-2]4-bromo-2-chlorobenzoic acid</strong> (0.15 g, 0.64 mmol) and bis(pinacolato)diboron (0.19 g, 0.76 mmol) in dioxane (30 mL) was added [1 ,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane (0.015 g, 0.019 mmol) and potassium acetate (0.18 g, 1.92 mmol). The reaction mixture was stirred at 80 0C for 5 h. After cooling to room temperature, ethyl acetate (10 mL) and water (10 mL) were added. The aqueous layer was extracted with ethyl acetate (2 x 20 mL). The organic portions were concentrated and recrystallized with hot hexanes to give the pure product (0.13 g, 69percent). MS(ES) m/e 283 [M+H]+

Reference： [1]Patent: WO2006/63167,2006,A1 .Location in patent: Page/Page column 31

2
[ 890839-31-3 ]
[ 1083326-19-5 ]
2-chloro-4-(5-(cyclopropanesulfonamido)pyridin-3-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80.0℃; for 16.0h;Inert atmosphere;	N-(5-bromopyridin-3-yl)cyclopropanesulfonamide (0.810 g, 2.92 mmol), sodium carbonate (1.24 g, 11.69 mmol) and 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)benzoic acid (0.991 g, 3.51 mmol) were combined in 1,4-dioxane (32 mL) and water (6.4 mL) followed by tetrakis(triphenylphosphine)palladium (0) (0.34 g, 0.292 mmol) to give a light yellow suspension. The suspension was placed under nitrogen and heated for 16 h at 80 C. The reaction was filtered through Celite and the solids washed with 1,4- dioxane followed by ethyl acetate. Concentrating the solvents obtained a pale yellow sticky solid. This was suspended in 50 mL of water and basified with 1 N NaOH solution until the pH was 12. The basic layer was washed once with 25 mL of ethyl acetate. After a back-extraction of the organic phase with 20 mL of water at pH=12, the combined basic phases were acidified with 1 N HC1 until pH=5 was reached. After standing overnight the precipitate was collected and dried to afford 2-chloro-4-(5-(cyclopropanesulfon- amido)pyridin-3-yl)benzoic acid (0.438 g, 1.24 mmol, 35%) as an off-white solid. MS (ESI, pos. ion) m/z: 353, 355 (M+l).

Reference： [1]Patent: WO2014/164749,2014,A1 .Location in patent: Page/Page column 314

3
[ 890839-31-3 ]
(R)-7-(3-aminopyrrolidin-1-yl)-4-chloroisoxazolo[5,4-c]pyridin-3-amine dihydrochloride salt [ No CAS ]
(R)-N-(1-(3-amino-4-chloroisoxazolo[5,4-c]pyridin-7-yl)pyrrolidin-3-yl)-2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 40.0℃; for 6.0h;	Step A.(R)-N-(1 -(3-Amino-4-chloroisoxazolo[5 ,4-clpyridin-7-yl)pyrrolidin-3-yl)-2-chloro-4-(4,4,5 ,5-tet ramethyl- 1,3 ,2-dioxaborolan-2-yl)benzamideTo a solution of (R)-7-(3 -aminopyrrolidin- 1 -yl)-4-chloroisoxazolo [5 ,4-c]pyridin-3 -aminedihydrochloride (0.92 mmol, 300 mg, EXAMPLE 11, Step E) and2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoic acid (1.0 mmol, 285 mg) in CH2C12 (6.0 mL) was added HATU (1.4 mmol, 524 mg) and DIPEA (2.8 mmol, 0.48 mL). The reaction mixture was stirred at 40 C for 6 h. Then the mixture was diluted with MeOH. The crude mixture was purified by 5i02 column chromatography (heptane:EtOAc = 50:50 to 0:100)to give the title compound.‘H NMR (400 MHz, DMSO-d6) 5 (ppm): 8.83 (1H, d, J= 6.4 Hz), 7.78 (1H, s), 7.62-7.59 (2H, m), 7.44 (1H, d, J= 7.3 Hz), 6.21 (2H, s), 4.58-4.50 (1H, m), 3.99-3.93 (1H, m), 3.87-3.74 (3H, m), 2.28-2.18 (1H, m), 2.09-2.00 (1H, m), 1.29 (12H, s)MS (ESI) mlz = 518, 520 (M+H)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2622 - 2628
[2]Patent: WO2015/160636,2015,A1 .Location in patent: Page/Page column 140

4
[ 890839-31-3 ]
(R)-N-(1-(3-amino-4-chloroisoxazolo[5,4-c]pyridin-7-yl)pyrrolidin-3-yl)-2-chloro-4-(pyrazin-2-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2015/160636,2015,A1

5
[ 890839-31-3 ]
(R)-N-(1-(3-amino-4-chloroisoxazolo[5,4-c]pyridin-7-yl)pyrrolidin-3-yl)-2-chloro-4-(6-oxo-1-(2,2,2-trifluoroethyl)-1,6-dihydropyridin-3-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2015/160636,2015,A1

6
[ 890839-31-3 ]
4-bromopyridazine hydrobromide [ No CAS ]
2-chloro-4-(pyridazin-4-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90.0℃; for 2.0h;	Step A. 2-Chloro-4-(pyridazin-4-yl)benzoic acidThe mixture of 2-chloro-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzoic acid (2.3 mmol,650 mg), 4-bromopyridazine hydrobromide (2.1 mmol, 500 mg), PdC12(dppf) (0.1 mmol, 76 mg),Cs2CO3 (10 mmol, 3.4 g) in 1,4-dioxane / water (15 mL / 15 mL) was degassed and heated at90 C for 2 h. The reaction mixture was poured into water (50 mL), washed with EtOAc (30 mL).The aqueous layer was adjusted to pH 3 using iN aq. HC1 and then the precipitate was filtered togive the title compound. MS (ESI) mlz = 235, 237 (M+H)‘H NMR (DMSO-d6) 5 (ppm): 9.71 (1H, dd, J= 2.5, 1.1 Hz), 9.34 (1H, dd, J 5.5, 0.9 Hz), 8.14(1H, d, J= 1.4 Hz), 8.11 (1H, dd, J= 5.5, 2.7 Hz), 7.98 (1H, dd, J 8.0, 1.6 Hz), 7.93 (1H, d, J8.2 Hz)

Reference： [1]Patent: WO2015/160636,2015,A1 .Location in patent: Page/Page column 137

7
[ 890839-31-3 ]
[ 1220039-64-4 ]
2-chloro-4-(pyridazin-4-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90.0℃; for 2.0h;	The mixture of 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid (2.3 mmol, 650 mg), 4-bromopyridazine hydrobromide (2.1 mmol, 500 mg), PdCl2(dppf) (0.1 mmol, 76 mg), Cs2C03 (10 mmol, 3.4 g) in 1,4-dioxane / water (15 mL / 15 mL) was degassed and heated at 90 C for 2 h. The reaction mixture was poured into water (50 mL), washed with EtOAc (30 mL). The aqueous layer was adjusted to pH 3 using IN aq. HC1 and then the precipitate was filtered to give the title compound. MS (ESI) m/z = 235, 237 (M+H) (0919) 1H NMR (DMSO-d6)

Reference： [1]Patent: WO2015/160634,2015,A1 .Location in patent: Page/Page column 123

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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
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H226	Flammable liquid and vapour
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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
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Code	Phrase
H300	Fatal if swallowed
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H311	Toxic in contact with skin
H312	Harmful in contact with skin
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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
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
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H361d	Suspected of damaging the unborn child
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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. 890839-31-3 ]

Quality Control of [ 890839-31-3 ]

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Product Details of [ 890839-31-3 ]

Safety of [ 890839-31-3 ]

Application In Synthesis of [ 890839-31-3 ]

[ 890839-31-3 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 890839-31-3 ]

Chlorides

Carboxylic Acids

Aryls

Organoboron

Esters

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 890839-31-3 ]