[ CAS No. 1263374-42-0 ] {[proInfo.proName]}

Name: 1263374-42-0|(2,3-Difluoropyridin-4-yl)boronic acid|98%
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SKU: A111167
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Quality Control of [ 1263374-42-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1263374-42-0 ]

SDS Specification

Alternatived Products of [ 1263374-42-0 ]

Product Details of [ 1263374-42-0 ]

CAS No. :	1263374-42-0	MDL No. :	MFCD12022339
Formula :	C₅H₄BF₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LJEFUOGGCMPGHN-UHFFFAOYSA-N
M.W :	158.90	Pubchem ID :	49761750
Synonyms :

Calculated chemistry of [ 1263374-42-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	33.98
TPSA :	53.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.29
Log Po/w (WLOGP) :	-0.12
Log Po/w (MLOGP) :	-0.48
Log Po/w (SILICOS-IT) :	-0.27
Consensus Log Po/w :	-0.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.35
Solubility :	7.17 mg/ml ; 0.0451 mol/l
Class :	Very soluble
Log S (Ali) :	-0.97
Solubility :	16.9 mg/ml ; 0.107 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.46
Solubility :	5.48 mg/ml ; 0.0345 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.17

Safety of [ 1263374-42-0 ]

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 [ 1263374-42-0 ]

* 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.

Upstream synthesis route of [ 1263374-42-0 ]
Downstream synthetic route of [ 1263374-42-0 ]

[ 1263374-42-0 ] Synthesis Path-Upstream 1~2

1
[ 1513-66-2 ]
[ 5419-55-6 ]
[ 1263374-42-0 ]

Reference： [1] Patent: US2011/28492, 2011, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2012/101066, 2012, A1, . Location in patent: Page/Page column 79

2
[ 1513-66-2 ]
[ 1263374-42-0 ]

Reference： [1] Patent: WO2012/101065, 2012, A2, . Location in patent: Page/Page column 138

[ 1263374-42-0 ] Synthesis Path-Downstream 1~10

1
[ 1513-66-2 ]
[ 5419-55-6 ]
[ 1263374-42-0 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 2,3-difluoropyridin-4-ylboronic acid (Intermediate W); A mixture of THF and hexanes (6 mL, 1:1 v:v), and diisopropyl amine (0.681 mL, 4.78 mmol) was cooled to -78 C. BuLi (2.5 M in hexanes, 2.00 mL, 5.00 mmol) was added to the cooled mixture, followed by addition of 2,3-difluoropyridine after about 15 minutes. The mixture was stirred for 1 hour at -78 C. before being transferred to a 3 mL THF solution of triisopropyl borate (1.11 mL, 4.78 mmol) at -78 C. via a cannula. The resulting solution was stirred at -78 C. for 1 hour, slowly warmed up to ambient temperature and then quenched with 2 M NaOH solution (20 mL). The two layers were separated and the aqueous phase was washed once with ether. The aqueous phase was then acidified with HCl to pH 5 and extracted three times with EtOAc. The organic layers were combined, dried over sodium sulfate and concentrated to yield the product as a light yellow solid, which was used in the next step without purification. LCMS (m/z): 159.9 (M+H), retention time=0.35 min.

Reference： [1]Patent: US2011/28492,2011,A1 .Location in patent: Page/Page column 27
[2]Patent: WO2012/101066,2012,A1 .Location in patent: Page/Page column 79

2
[ 1263374-42-0 ]
[ 1346815-35-7 ]
[ 1346817-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride;Pd-132; In methanol; water; at 80℃;	EXAMPLE 1292',3'-difluoro-5-{(1 R)-1 -[5-fluoro-2-(2H-1 ,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-6- amine Chiral5-Bromo-3-[(R)-1-(5-fluoro-2-[1 ,2,3]triazol-2-yl-phenyl)-ethoxy]-pyridin-2-ylamine(example 45) (200 mg, 0.529 mmol, 1.0 eq) and <strong>[1263374-42-0]2,3-difluoropyridin-4-ylboronic acid</strong> (168 mg, 1.06 mmol, 2.0 eq) were dissolved in eOH (5 mL), followed by the addition of freshly prepared aqueous solution of CsF (563mg, 3.5 mmol, 7 eq) in water (3.34 mL) and Pd-132 (64 mg, 0.09 mmol, 0.17eq), then degassed for three times. The mixture was heated up to 80C for overnight. LCMS showed >80% conversion to desired product, and ~10% of des-bromation of example 45. The reaction mixture was filtered. The filtrate was concentrated and purified via a Biotage silica gel cartridge to provide the title compound (174 mg) as a white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 8.21 - 8.23 (m, 2 H) 8.00 (d, J=5.05 Hz, 1 H) 7.91 (t, J=1.77 Hz, 1 H) 7.70 (dd, J=9.73, 2.91 Hz, 1 H) 7.64(dd, J=8.84, 5.05 Hz, 1 H) 7.33 - 7.37 (m, 2 H) 6.87 (s, 1 H) 6.57 (s, 2 H) 5.59 (q, 1 H) 1.62 (d, J=6.32 Hz, 3 H).

Reference： [1]Patent: WO2011/138751,2011,A2 .Location in patent: Page/Page column 171-172

3
[ 1263374-42-0 ]
[ 1346815-35-7 ]
[ 1346817-03-5 ]

Reference： [1]Patent: WO2011/138751,2011,A2

4
[ 1263374-42-0 ]
[ 1394312-68-5 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6187 - 6190

5
[ 1263374-42-0 ]
[ 126-30-7 ]
C₁₀H₁₂BF₂NO₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6187 - 6190

6
[ 1263374-42-0 ]
[ 126-30-7 ]
C₁₁H₁₅BF₂NO₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6187 - 6190

7
[ 1513-66-2 ]
[ 1263374-42-0 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of THF and hexanes (6mL, 1 : 1 v:v), and diisopropyl amine (0.681 mL, 4.78 mmol) was cooled to -78 C. BuLi (2.5 M in hexanes, 2.00 mL, 5.00 mmol) was added to the cooled mixture, followed by addition of 2,3-difluoropyridine after about 15 minutes. The mixture was stirred for 1 hour at -78 C before being transferred to a 3 mL THF solution of triisopropyl borate (1 .1 1 mL, 4.78 mmol) at -78 C via a cannula. The resulting solution was stirred at -78 C for 1 hour, slowly warmed up to ambient temperature and then quenched with 2 M NaOH solution (20 mL). The two layers were separated and the aqueous phase was washed once with ether. The aqueous phase was then acidified with HCI to pH 5 and extracted three times with EtOAc. The organic layers were combined, dried over sodium sulfate and concentrated to yield the product as a light yellow solid, which was used in the next step without purification. LCMS (m/z): 159.9 (M+H), retention time = 0.35 min.

Reference： [1]Patent: WO2012/101065,2012,A2 .Location in patent: Page/Page column 138

8
[ 1263374-42-0 ]
[ 1453852-22-6 ]
2',3'-difluoro-N-(tetrahydro-2H-pyran-4-yl)-[4,4'-bipyridin]-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;	[00209] Step 2: A mixture of 4-bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine (294 mg, 1.14 mmol), <strong>[1263374-42-0](2,3-difluoropyridin-4-yl)boronic acid</strong> (200 mg, 1.26 mmol), PdCl2(dppf)*dcm (47 mg, 0.057 mmol) and Na2COs 20% aqueous (1.15 mL, 2.29 mmol) in dioxane (5.7 mL, 1.14 mmol) was heated to 90 C with stirring for 18 hours and allowed to cool to room temperature. The mixture was diluted with EtOAc (50 mL) and washed with brine (20 mL). The organic layer was dried (MgS04), filtered and concentrated in vacuo. The crude isolated was purified by flash chromatography on silica gel (Ready Sep 40 g) eluting with a gradient of 0-6% MeOH:DCM (20 CV) and then crystallized from MeOH to provide 2',3'-difluoro-N-(tetrahydro-2H-pyran-4-yl)-[4,4'-bipyridin]-2-amine (210 mg, 63.0% yield) as a solid. LCMS (APCI+) m/z 292.1 (M+l).

Reference： [1]Patent: WO2015/103137,2015,A1 .Location in patent: Paragraph 00209

9
[ 1263374-42-0 ]
(1R,2R,3S,5R)-6,6-dimethyl-2-(2,5,8,11-tetraoxatridecan-13-yl)bicyclo[3.1.1]heptane-2,3-diol [ No CAS ]
C₂₃H₃₄BF₂NO₆ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 3909 - 3913
Angew. Chem.,2016,p. 3977 - 3981,5

10
[ 1263374-42-0 ]
C₂₉H₂₀BrN₃ [ No CAS ]
C₃₄H₂₂F₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 120℃; for 6h;	To a mixture of degassed 1 ,4-dioxane (3.1 mL) and water (0.72 mL) in a microwave vial was added [1 ,T-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane (0.006 g, 0.0072 mmol), followed by the title compound from Preparative Example B (0.07 g, 0.148 mmol), <strong>[1263374-42-0](2,3-difluoropyridin-4-yl)boronic acid</strong> (0.028 g, 0.176 mmol) and cesium carbonate (0.096 g, 0.29 mmol). The reaction mixture was then heated at ~120C in a sand-bath for 6 hours. The reaction mixture was diluted with ethyl acetate (60 mL) and water (20 mL), the organic phase was separated, dried over Na2S04, filtered and the solvents were evaporated in vacuo. The dark residue was purified by chromatography on silica (12 g, puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford the title compound together with -10% of Preparative Example B as a colorless glass (0.0223 g, 29.7 %). (0292) Title compound: 1H-NMR (400 MHz, CDCI3) d = 9.31 (s, 1 H), 8.46 (d, 1 H), 8.29 (d, 1 H), 7.99 (dd, 1 H), 7.73 (dd, 1 H), 7.57-7.53 (m, 5H), 7.32-7.24 (m, 10H), 6.85 (t, 1 H), 6.56 (dd, 1 H)

Reference： [1]Patent: WO2019/145292,2019,A1 .Location in patent: Page/Page column 48; 49

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P321
P322
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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.
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Physical hazards
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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
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
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H351	Suspected of causing cancer
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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. 1263374-42-0 ] {[proInfo.proName]}

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[ 1263374-42-0 ] Synthesis Path-Upstream 1~2

[ 1263374-42-0 ] Synthesis Path-Downstream 1~10

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Fluorinated Building Blocks

Organoboron

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Pyridines

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[ 1263374-42-0 ]

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[ 1263374-42-0 ]