[ CAS No. 908350-80-1 ] {[proInfo.proName]}

Name: 908350-80-1|2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine|95%
Brand: Ambeed
SKU: A106309
Price: 5.0 USD
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Quality Control of [ 908350-80-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 908350-80-1 ]

SDS Specification

Alternatived Products of [ 908350-80-1 ]

Product Details of [ 908350-80-1 ]

CAS No. :	908350-80-1	MDL No. :	MFCD11973624
Formula :	C₁₇H₂₀BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CMGIUUPUDMXXLT-UHFFFAOYSA-N
M.W :	281.16	Pubchem ID :	53482118
Synonyms :

Calculated chemistry of [ 908350-80-1 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.35
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	86.15
TPSA :	31.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.08
Solubility :	0.0234 mg/ml ; 0.0000834 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.84
Solubility :	0.0405 mg/ml ; 0.000144 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.14
Solubility :	0.000205 mg/ml ; 0.000000728 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.02

Safety of [ 908350-80-1 ]

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 [ 908350-80-1 ]

* 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 [ 908350-80-1 ]
Downstream synthetic route of [ 908350-80-1 ]

[ 908350-80-1 ] Synthesis Path-Upstream 1~2

1
[ 61676-62-8 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;	To a solution of 2-(4'-bromophenyl)pyridine (0.468 g, 2 mmol). in anhydrous THF (10 ml) was added dropwse n-BuL (3 ml, 3.6 mmol) at -78"C The reaction was stirred 1 h, then 2-isopropoxy-4,4,5_>5-tetramethyl-l,3,2-dioxaborolane (0.52 ml, 2.5 mmol) was added. The mixture was stirred overnight. Then Hie reaction was quenched with water and extracted with dchloromethane (30 ml) 3 times. The organic layer was -washed with brine and dried over MgSO₄ and concentrated in vacuo. After column chromatography (silica gel, ethyl acetate: hexane = 1: 20) to give product 0.22 g (39percent).

Reference： [1] Patent: WO2006/93466, 2006, A1, . Location in patent: Page/Page column 40

2
[ 63996-36-1 ]
[ 73183-34-3 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium acetate; tricyclohexylphosphine In 1,4-dioxane for 20 h; Inert atmosphere; Reflux	1. Preparation of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)pyridine 0.39 g (0.4 mmol) of Pd(dba)₃ and 0.28 g (1 mmol) of tricyclohexylphosphine are suspended in 10 ml of dry dioxane under a nitrogen atmosphere. The resulting mixture is stirred at room temperature for 30 minutes. Subsequently, 5.3 g (15 mmol) of bis(pinacolato)diboron, 2.1 g (21 mmol) of KOAc and 3.3 g (14 mmol) of 2-(4-bromophenyl)pyridine are added gradually. The reaction mixture is boiled under reflux for 20 hours, cooled and treated with 10 ml of water at room temperature. The product is extracted with dichloromethane. The solvent is removed under reduced pressure and the resulting crude product is purified by means of a short silica gel column. After purification by means of the silica gel column (dichloromethane/hexane, 3:1), 82percent of the desired product is obtained. ¹H NMR(CDCl₃): δ=1.37(s,12H), 7.22-7.26(m, 1H), 7.72-7.80(m, 2H), 7.92(J=8.4 Hz, 2H), 8.02(J=8.2Hz, 2H), 8.71(J=4.9 Hz, 1H).
11.2 g	for 2 h; Inert atmosphere; Reflux	First, a solution was added cyclopentyl methyl ether (CPME) in (64 ml) 2-(4- bromophenyl) pyridine (15 g) and bis (pinacolato) diboron (19.5 g), under a nitrogen atmosphere, palladium acetate (Pd ( OAc) 2) (0.4g), triphenylphosphine (PPh3) (1.5g) and potassium acetate (AcOK) (18.9g) was added with stirring at room temperature. After stirring for 2 hours at reflux temperature, the reaction mixture was cooled to room temperature, was added with ethylenediaminetetraacetic acid (EDTA) solution (35 ml) in toluene (500ml). The organic matter to remove salts by water washing operation was purified with activated carbon column chromatography (toluene). There was thus obtained 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine (11.2 g).

Reference： [1] Patent: US2013/231489, 2013, A1, . Location in patent: Paragraph 0184; 0185
[2] Patent: JP5673362, 2015, B2, . Location in patent: Paragraph 1082; 1084

[ 908350-80-1 ] Synthesis Path-Downstream 1~43

1
[ 61676-62-8 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
39%		To a solution of 2-(4'-bromophenyl)pyridine (0.468 g, 2 mmol). in anhydrous THF (10 ml) was added dropwse n-BuL (3 ml, 3.6 mmol) at -78"C The reaction was stirred 1 h, then 2-isopropoxy-4,4,5>5-tetramethyl-l,3,2-dioxaborolane (0.52 ml, 2.5 mmol) was added. The mixture was stirred overnight. Then Hie reaction was quenched with water and extracted with dchloromethane (30 ml) 3 times. The organic layer was -washed with brine and dried over MgSO4 and concentrated in vacuo. After column chromatography (silica gel, ethyl acetate: hexane = 1: 20) to give product 0.22 g (39%).

Reference： [1]Patent: WO2006/93466,2006,A1 .Location in patent: Page/Page column 40

2
[ 908350-80-1 ]
[ 393841-81-1 ]
[ 908350-98-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene;Heating / reflux;	A mixture of 2-bromo-(2';7'-di-tert-butyl)-9,9'-sphiiro-bitluorene (0.35 g, 0.7 mmol), compound - ^ 10 (0.22g, 0.78 mtnol). tetrakis(triphenylpliosphme)palladium(0) . (0-036 g, 0.03 mmol), aqueous sodium carbonate (2 M, 0.5 ml), ethanol (0.5 ml), toluene (4 ml) was deoxygenated and then heated to reflux under nitrogen, stirring overnight After cooling to room temperature, the mixture was washed with water and extracted with ethyl acetate (20 ml) 3 times. The organic layer was then washed with brine and dried over MgSO4 and concentrated in vacuo. After column chromatography (silica gel, ethyl acetate: hexane = 1: 5) to give G 0.26g (64%). 1H NMR (400 MHz, chloroform-d): delta, ppm 8.7 (s, 1 H), 7.966 (t.3 H), 7.92 (d, 1 H)5 7.76,2 (m, 5 H), 7.59 (d, 2 H), 7.42 (d, 3 H), 7278 (d, 1 H), 7.13 (t, 1 H), 7.044 (s, IH), 6.724 (d, 3 H)7 1.17 (s, 18 H).

Reference： [1]Patent: WO2006/93466,2006,A1 .Location in patent: Page/Page column 40-41; Sheet 13

3
[ 846563-95-9 ]
[ 908350-80-1 ]
C₂₄H₁₆FN₃O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1272 - 1276

4
[ 908350-80-1 ]
[ 1133023-55-8 ]
C₁₅₆H₁₁₇N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.2%	With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux;	1.2 g (0.64 mmol) of M-3, 0.72 g (2.57 mmol) of 1-(4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborane-2-yl)phenyl)pyridine, and 0.05g of tetrakistriphenylphosphine palladium were dissolved in 30 ml_ of tetrahydrofuran (THF) under an argon atmosphere in a 250ml round flask with a thermometer, a reflux condenser, and an agitator. 15ml_ of 20% tetratriethyl ammonium hydroxide was added thereto. The resulting mixture was refluxed for reaction at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature, and was then extracted several times with methylenechloride and washed with water. <n="89"/>Then, anhydrous magnesium sulfate was used to remove moisture from the washed reactant. The resulting product was filtered to remove the solvent.The reactant with no solvent was purified through a silica gel column using a mixed solvent of methylenechloride/methanol in a ratio of9:1 and recrystallized by a mixed solvent of methylenechloride/ethylacetate in a ratio of 94:6, obtaining 0.7 g (52.2%) of white CISH-4.

Reference： [1]Patent: WO2009/35295,2009,A2 .Location in patent: Page/Page column 86-87

5
[ 26032-72-4 ]
[ 908350-80-1 ]
[ 1214276-57-9 ]

Yield	Reaction Conditions	Operation in experiment
67.9%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; toluene; for 12h;Reflux;	2.3 g (10 mmol) of intermediate product (A), 6.3 g (22 mmol) of 2-(4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyridine (B), and 0.6 g (0.5 mmol) of tetrakis-(triphenylphosphine)palladium were suspended in a mixed solvent of 70 ml of tetrahydrofuran and 50 ml of toluene to provide a suspension. The suspension was added to a solution in which 5.7 g (41 mmol) of potassium carbonate was dissolved in 50 ml of water. The obtained mixture was heated and refluxed for 12 hours. After separating the reaction fluid into two layers, an organic layer was washed with a saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate.<ii6> The organic solvent was distillated and removed under reduced pressure, and then the residue was recrystallized with toluene. The obtained crystal was separated by filtration and washed with toluene to obtain 3.9 g (yield: 67.9 %) of compound (1).<ii7> 1H NMR (300MHz, CDCl3) 8.85 (d,2H), 8.75 (d,2H), 8.45 (d,2H), 8.34(d,2H), 8.21 (m,4H), 8.08 (s.lH), 7.80 (m,4H), 7.60 Gn13H), 7.27 (m,2H);MS[M+1] 463.

Reference： [1]Patent: WO2010/24572,2010,A2 .Location in patent: Page/Page column 21-22

6
[ 908350-80-1 ]
[ 1214278-10-0 ]
[ 1214276-59-1 ]

Yield	Reaction Conditions	Operation in experiment
69.0%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; toluene; for 12h;Reflux;	3.2 g (12 mmol) of intermediate product (C), 7.2 g (26 mmol) of 2-(4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyridine (B), and 0.7 g (0.6 mmol) of tetrakis-(triphenylrhohosphine)palladium were suspended in a mixed solvent of 100 ml of tetrahydrofuran and 65 ml of toluene to provide a suspension. The suspension was added to a solution in which 6.4 g (47 mmol) of potassium carbonate was dissolved in 65 ml of water. The obtained mixture was heated and refluxed for 12 hours. After separating the reaction fluid into two layers, an organic layer thereof was washed with a saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate.<127> The organic solvent was disti Hated and removed under reduced pressure, and then the residue was recrystallized with toluene. The extracted crystal was separated by filtration and washed with toluene to obtain 4.1 g (yield: 69.0 %) of compound (2).<128> 1H NMR (300MHz, CDCl3) 8.85 (d,2H), 8.76 (d,2H), 8.45 (m,3H), 8.20(m,4H), 8.01 (m,3H), 7.80 (m,5H), 7.61 (m,3H), 7.27 (m,2H); MS[M+1] 513.

Reference： [1]Patent: WO2010/24572,2010,A2 .Location in patent: Page/Page column 22-24

7
[ 908350-80-1 ]
[ 1312478-57-1 ]
[ 1358778-92-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1662 - 1670

8
[ 908350-80-1 ]
[ 2298-07-9 ]
[ 1383803-84-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 85℃; for 12h;	30.0 g (135.1 mmol) of 1-amino-4-bromonaphthalene, 41.8 g (148.6 mmol) of <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong>, and 3.9 g (3.4 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 900 ml of a toluene solvent. A solution in which 37.3 g (270.2 mmol) of potassium carbonate (K2CO3) was dissolved in 300 ml of water was added thereto, and then they were reacted at 85 C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was separated by a column and dried to provide a yellow solid of an intermediate product (I) in 24.9 g (yield: 62%).

Reference： [1]Patent: US2012/280613,2012,A1 .Location in patent: Page/Page column 272

9
[ 908350-80-1 ]
[ 1383803-86-8 ]

Reference： [1]Patent: US2012/280613,2012,A1

10
[ 908350-80-1 ]
[ 1383800-62-1 ]

Reference： [1]Patent: US2012/280613,2012,A1

11
[ 908350-80-1 ]
[ 1383803-68-6 ]
[ 1383803-88-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; for 12h;	14.0 g (32.9 mmol) of intermediate product (C), 10.2 g (36.3 mmol) of 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 280 ml of a tetrahydrofuran (THF) solvent. http://www.splashdivecenter.com/ 9.1 g (66.0 mmol) of potassium carbonate (K2CO3) was dissolved in 140 ml of water was added thereto, and then they were reacted at 80 C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a pale yellow solid of intermediate product (K) in 9.7 g (yield: 54%).

Reference： [1]Patent: US2012/280613,2012,A1 .Location in patent: Page/Page column 273-274

12
[ 908350-80-1 ]
[ 1383803-69-7 ]
[ 1383794-95-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 90℃; for 12h;	14.9 g (26.3 mmol) of intermediate product (C), 8.9 g (31.6 mmol) of 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 0.9 g (0.8 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 7.3 g (52.6 mmol) of potassium carbonate (K2CO3) was dissolved in 150 ml of water was added thereto, and then they were reacted at 90 C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 13.9 g (yield: 77%). (calculation value: 684.82, measurement value: MS[M+1] 685.25)

Reference： [1]Patent: US2012/280613,2012,A1 .Location in patent: Page/Page column 273

13
[ 908350-80-1 ]
[ 1407504-40-8 ]
[ 1383795-47-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 90℃; for 12h;	15.0 g (32.2 mmol) of the intermediate product (N), 10.9 g (38.6 mmol) of <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong>, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 8.9 g (64.4 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and then they were reacted at 90 C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 16.5 g (yield: 88%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)

Reference： [1]Patent: US2012/280613,2012,A1 .Location in patent: Page/Page column 276-277

14
[ 63996-36-1 ]
[ 73183-34-3 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; for 20h;Inert atmosphere; Reflux;	1. Preparation of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)pyridine 0.39 g (0.4 mmol) of Pd(dba)3 and 0.28 g (1 mmol) of tricyclohexylphosphine are suspended in 10 ml of dry dioxane under a nitrogen atmosphere. The resulting mixture is stirred at room temperature for 30 minutes. Subsequently, 5.3 g (15 mmol) of bis(pinacolato)diboron, 2.1 g (21 mmol) of KOAc and 3.3 g (14 mmol) of 2-(4-bromophenyl)pyridine are added gradually. The reaction mixture is boiled under reflux for 20 hours, cooled and treated with 10 ml of water at room temperature. The product is extracted with dichloromethane. The solvent is removed under reduced pressure and the resulting crude product is purified by means of a short silica gel column. After purification by means of the silica gel column (dichloromethane/hexane, 3:1), 82% of the desired product is obtained. 1H NMR(CDCl3): delta=1.37(s,12H), 7.22-7.26(m, 1H), 7.72-7.80(m, 2H), 7.92(J=8.4 Hz, 2H), 8.02(J=8.2Hz, 2H), 8.71(J=4.9 Hz, 1H).
78%	In 1,4-dioxane; at 110℃;	II) Take 300mg Compound 2 and 360mgofPinacol diborate,20mL of dioxane was added to a single-necked bottle with a stir bar, and refluxed at 110 C overnight.At the end of the reaction, extract with dichloromethane to retain the organic phase,Compound 3 was obtained by column chromatography with a yield of 78%;
11.2 g	With potassium acetate; palladium diacetate; triphenylphosphine; for 2h;Inert atmosphere; Reflux;	First, a solution was added cyclopentyl methyl ether (CPME) in (64 ml) 2-(4- bromophenyl) pyridine (15 g) and bis (pinacolato) diboron (19.5 g), under a nitrogen atmosphere, palladium acetate (Pd ( OAc) 2) (0.4g), triphenylphosphine (PPh3) (1.5g) and potassium acetate (AcOK) (18.9g) was added with stirring at room temperature. After stirring for 2 hours at reflux temperature, the reaction mixture was cooled to room temperature, was added with ethylenediaminetetraacetic acid (EDTA) solution (35 ml) in toluene (500ml). The organic matter to remove salts by water washing operation was purified with activated carbon column chromatography (toluene). There was thus obtained 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine (11.2 g).

Reference： [1]Patent: US2013/231489,2013,A1 .Location in patent: Paragraph 0184; 0185
[2]Patent: CN110845544,2020,A .Location in patent: Paragraph 0024; 0025; 0026; 0031; 0032
[3]Patent: JP5673362,2015,B2 .Location in patent: Paragraph 1082; 1084

15
potassium hydrogen difluoride [ No CAS ]
[ 908350-80-1 ]
potassium 4-(pyridin-2-yl)phenyl trifluoroborate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14012 - 14015

16
[ 908350-80-1 ]
[ 58861-53-3 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14012 - 14015

17
[ 908350-80-1 ]
C₉H₆BrNO₃S [ No CAS ]
C₂₀H₁₄N₂O₃S [ No CAS ]

Reference： [1]Synlett,2015,vol. 26,p. 1496 - 1500

18
[ 908350-80-1 ]
[ 19226-36-9 ]
N-(2-(pyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 16395 - 16399

19
[ 908350-80-1 ]
9-([1,1'-biphenyl]-3-yl)-2,7-dibromo-9H-carbazole [ No CAS ]
9-([1,1'-biphenyl]-3-yl)-2,7-bis(4-(pyridin-2-yl)phenyl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.3 g	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; for 8h;Inert atmosphere; Reflux;	First, using a palladium catalyst, with 2-(4-bromophenyl)pyridine and bis(pinacolato)diboron to coupling reaction, <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> was synthesized. Then, 9 -([1,1'-biphenyl]-3-yl)-2,7-dibromo-9H-carbazole (1.5g), <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> (1.8 g), to a flask containing potassium carbonate (1.7 g) and PdCl2{P(t-Bu)2-(p-NMe2-Ph)}2 (Johnson Matthey Inc., Pd-132) (0.06 g), charged with toluene (15 ml) and water (3 ml), under argon, this mixture was was stirred for 8 hours at reflux temperature. The reaction mixture was cooled to room temperature, water and chloroform were added for liquid separation. The chloroform was distilled off under reduced pressure, the resulting solid amino group-modified silica gel was purified by (NH DM1020 Fuji Silysia Co.) column chromatography (heptane / toluene = 1/2 (volume ratio)). The solvent was distilled off under reduced pressure, washed with ethyl acetate, finally, a compound represented by the formula (1-1-1198), 9-([1,1'-biphenyl]-3-yl)-2,7-bis(4-(pyridin-2-yl)phenyl)-9H-carbazole (0.3 g).
0.3 g	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; for 8h;Inert atmosphere; Reflux;	First, using a palladium catalyst, 2-(4-bromophenyl)pyridine and bis Pinacolate diboron were done coupling reaction, and <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> was synthesized. Then, to flask containing 9-([1,1'-biphenyl]-3-yl)-2,7-dibromo-9H-carbazole (1.5g), <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> (1.8 g), potassium carbonate (1.7 g) and PdCl2{P(t-Bu)2-(p-NMe2-Ph)}2 (Johnson Matthey Co.,Pd-132) (0.06 g), under argon atmosphere, toluene (15 ml) and water (3 ml) were put, and stirred for 8 hours at reflux temperature. The reaction mixture was cooled toroom temperature, and water and chloroform were added and liquid separated. The chloroform was distilled off under reduced pressure, and the resulting solid was purified by amino group-modified silica gel (NH DM1020 : Fuji Silysia Co.) column chromatography (heptane / toluene = 1/2 (volume ratio)). The solvent wasdistilled off under reduced pressure, then washed with ethyl acetate, and finally,a compound represented by the formula (1-1-1198), 9-([1,1'-biphenyl]-3-yl)-2,7-bis(4-(pyridin-2-yl)phenyl)-9H-carbazole (0.3 g) was obtained.

Reference： [1]Patent: JP5949354,2016,B2 .Location in patent: Paragraph 0390; 0392
[2]Patent: JP5783173,2015,B2 .Location in patent: Paragraph 0431; 0433

20
[ 908350-80-1 ]
7-phenyl-7H-benzo[c]carbazole-5,9-diyl bis(trifluoromethanesulfonate) [ No CAS ]
7-phenyl-5,9-bis(4-(pyridin-2-yl)phenyl)-7H-benzo[c]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.2 g	With potassium phosphate; palladium diacetate; triphenylphosphine; In tetrahydrofuran; isopropyl alcohol; for 5h;Inert atmosphere; Reflux;	Then, above-obtained 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine and (6.9 g), 7-phenyl--7H- benzo [c] carbazole-5,9-diyl bis (trifluoromethanesulfonate) THF / isopropyl alcohol containing (6.6 g) (IPA) solution (by volume 3: 1) (37ml ) in a nitrogen atmosphere, palladium acetate (0.1 g), triphenylphosphine (0.3 g) and tripotassium phosphate and (K3PO4) (9.4g) was added with stirring at room temperature. After stirring for 5 hours at reflux temperature, the reaction mixture was cooled to room temperature, was added with ethylenediaminetetraacetic acid (EDTA) solution (50ml) in toluene (500ml). The organic matter to remove salts by water washing operation was purified with activated charcoal column chromatography (toluene / ethyl acetate = 10/1 (volume ratio)), a compound represented by formula (1-10) 7-phenyl--5 to give 9- bis (4- (pyridin-2-yl) phenyl)-7H-benzo [c] carbazole (1.2 g).

Reference： [1]Patent: JP5673362,2015,B2 .Location in patent: Paragraph 1083; 1084

21
[ 908350-80-1 ]
7-(naphthalen-1-yl)-7H-benzo[c]carbazole-5,9-diyl bis(trifluoromethanesulfonate) [ No CAS ]
7-(naphthalen-1-yl)-5,9-bis(4-(pyridin-2-yl)phenyl)-7H-benzo[c]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With potassium phosphate; triphenylphosphine; In water; tert-butyl alcohol; for 10h;Inert atmosphere; Reflux;	Under a nitrogen atmosphere, as above-obtained 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine (8.4 g), 7- (naphthalene-1-yl) -7H- benzo [c] carbazole-5,9-diyl bis (trifluoromethanesulfonate) (6.4g), tripotassium phosphate (8.5g), Pd (PPh3) 4 (1.1 g), pseudo cumene (1,2,4-trimethylbenzene) (75 ml), and stirred for 10 hours the flask containing the reflux temperature of t- butyl alcohol (5 ml) and water (1 ml). The reaction mixture was cooled to room temperature and ethylenediaminetetraacetic acid (EDTA) aqueous solution and toluene were added for liquid separation. The solid obtained by evaporation of the solvent under reduced pressure was subjected to hot filtration was heated and dissolved in chlorobenzene. The solid obtained and the solvent was distilled off under reduced pressure and recrystallized from chlorobenzene, a compound represented by the formula (1-8710) 7 (naphthalen-1-yl) 5,9-bis (4- ( pyridin-2-yl) to yield phenyl)-7H-benzo [c] carbazole (1.8 g).

Reference： [1]Patent: JP5673362,2015,B2 .Location in patent: Paragraph 1119; 1120

22
[ 908350-80-1 ]
C₄₆H₂₈ClN₂OP [ No CAS ]
C₅₇H₃₆N₃OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; for 8h;Reflux;	Compound E(4.2 g, 15 mmol) and 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)Was added to 100 mL of dioxane. 50 ml of 2.0 M K3CO4 and 0.1 g of Pd (PtBu3) 2 were added, and the mixture was refluxed with stirring for 8 hours.The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-74].(8.0 g, yield 66%,

Reference： [1]Patent: KR2016/45612,2016,A .Location in patent: Paragraph 0238

23
[ 908350-80-1 ]
C₉H₆BrNO₄ [ No CAS ]
methyl 2-(5-(4-(pyridin-2-yl)phenyl)furan-2-yl)oxazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In water; for 24h;Reflux; Inert atmosphere;	General procedure: To a 20-mL Schlenktube equipped with a magnetic stirring bar were added 2 (386.3 mg, 2.0 mmol) and 1,2-dimethoxyethane(7 mL) under nitrogen atmosphere. After cooling to 0 C, N-bromosuccinimide (NBS, 195.8 mg, 1.1mmol) was added and the resulting mixture was stirred at 0 C for 1 h. NBS (117.5 mg, 0.66 mmol) wasfurther added to the reaction mixture and the solution was stirred at 0 C for 1 h. Another NBS (117.5 mg,0.66 mmol) was added again and further stirring was continued for 2 h. The reaction mixture warmed toroom temperature. To the solution were added <strong>[908350-80-1]4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylpyridine</strong>(674.8 mg, 2.4 mmol), aqueous potassium carbonate (2 M, 6 mmol), and PdCl2(PPh3)2 (70.2 mg,0.10 mmol), successively. The mixture was allowed to stir under reflux for 24 h. After cooling to roomtemperature, the mixture was poured into the mixture of CH2Cl2/water and the two phases were separated.Aqueous layer was extracted with CH2Cl2 three times and the combined organic layer was dried overanhydrous sodium sulfate and concentrated under reduced pressure to leave a crude solid, which waspurified by recrystallization (CHCl3/MeOH)

Reference： [1]Heterocycles,2016,vol. 93,p. 140 - 149

24
[ 908350-80-1 ]
2-(4-[18F]fluorophenyl)pyridine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276

25
[ 908350-80-1 ]
6-(bromomethyl)-7-(4-methoxybenzyl)-3-(tetrahydro-2H-pyran-4- yl)imidazo[1,5-a]pyrazin-8(7H)-one [ No CAS ]
7-[(4-methoxyphenyl)methyl]-6-[[4-(2-pyridyl)phenyl]methyl]-3-tetrahydropyran-4-ylimidazo[1,5-a]pyrazin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	Six identical reactions were run in parallel: A mixture of 6-(bromomethyl)-7-(4-methoxybenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one (500 mg, 1.16mmol), <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> (489 mg, 1.74mmol), K2C03 (321 mg, 2.32 mmol), Pd(dppf)C12 (170 mg, 0.23 mmol) in dioxane (40 mL) andwater (1.50 mL) were degassed and purged with N2 3 times, then the mixture was stirred at 100C for 12 hours under an atmosphere of N2. The six reaction mixtures were combined and concentrated under reduced pressure to remove dioxane and water. The residue was purified by preparative-TLC on silica gel (ethyl acetate) followed by preparative-HPLC to give7-[(4-methoxyphenyl)methyl]-6-[[4-(2-pyridyl)phenyl]methyl]-3-tetrahydropyran-4-yl-imidazo[1,5-a]pyrazin-8-one. 1H NMR (CDCI3 400 MHz): 6 8.71(d, i = 4.8 Hz, 1H), 8.01(d, i =8.0 Hz, 2H), 7.97 (s, 1H), 7.81 - 7.23(m, 2H), 7.29(s, 2H), 7.27 (s, 1H), 7.11 (d, i = 8.4 Hz, 2H),6.87 (d, i = 8.4 Hz, 2H), 6.76 (s, 1H), 5.03 (s, 2H), 4.12 -4.10 (m, 2H), 3.84 (s, 2H), 3.80 (s, 3H),3.55 (t,i = 10.0 Hz, 2H), 3.10-3.04 (m, 1H), 2.19-2.09 (m, 2H), 1.90-1.87 (m, 2H). LC-MS: tR= 0.49 mm (Method A), m/z = 507.1 [M + H]t

Reference： [1]Patent: WO2018/73251,2018,A1 .Location in patent: Page/Page column 60; 61

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 - 100℃;	General procedure: After the bromine compound (1 equivalent) was dissolved in DMF,Bis (pinacolato) diboron (1.1 eq.), Pd (dppf) Cl2 (0.03 mmol)After addition of KOAc (3 eq) And stirred at 90 to 100 C. When the reaction was complete, DMF was removed by distillation and extracted with CH2Cl2 and water.The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to give product Sub2.

27
[ 908350-80-1 ]
C₂₄H₁₃BrN₄ [ No CAS ]
C₃₅H₂₁N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.1 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 16h;Inert atmosphere; Reflux;	The specific operation process is: in a 100mL three-necked flask,Compound D01 (1.75 g, 0.004 mol) was added.Compound E01 (1.12 g, 0.004 mol),Potassium carbonate (0.55 g, 0.004 mol),Toluene (36g), deionized water (15g),Under the protection of nitrogen, the catalyst Pd(PPh3)4 (0.1g) was added.The temperature is raised to reflux, the reaction is kept for 16 hours, and the temperature is lowered to 40 C.The liquid phase was extracted once with 50 mL of tetrahydrofuran, the organic phase was combined, and the solvent was evaporated. The obtained crude product was purified by silica gel column chromatography.Petroleum ether = 1:1 (volume ratio), the target product C01 crude product 1.4g,Further sublimation purification using a chemical vapor deposition system,Sublimation temperature 315 C, get 1.1g target C01 boutique,

Reference： [1]Patent: CN108822114,2018,A .Location in patent: Paragraph 0039-0042

28
[ 4467-06-5 ]
[ 73183-34-3 ]
[ 908350-80-1 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 5392 - 5395
Angew. Chem.,2019,vol. 131,p. 5446 - 5449,4

29
[ 908350-80-1 ]
2-chloro-4-phenyl-6-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,5-triazine [ No CAS ]
2-phenyl-4-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-6-(4-(pyridin-2-yl)phenyl)-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 23h;Inert atmosphere; Reflux;	A flask was flushed with nitrogen and charged with 6 2-chloro-4-phenyl-6-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,5-triazine (7.4 g, 14.6 mmol), 16 <strong>[908350-80-1]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> (4.71 g, 16.75 mmol), 8 Pd(PPh3)4 (0.34 g, 0.29 mmol), and 9 K2CO3 (4.03 g, 29 mmol). A mixture of deaerated 10 THF/11 water (2:1, 90 mL) was added and the reaction mixture was heated to reflux under a nitrogen atmosphere for 23 h. After cooling down to 5 C., the resulting precipitate was isolated by suction filtration and washed with THF and n-hexane. The obtained white solid was dissolved in 13 chloroform and washed with water three times. After drying over MgSO4, the organic phase was filtered over a pad of Florisil. After rinsing with additional chloroform, the colorless filtrate was concentrated in vacuo to a minimal volume and 14 n-hexane was added. After stirring for 30 min., the resulting white 17 precipitate was isolated by suction filtration and washed with n-hexane. Further purification was achieved by column chromatography (silica, chloroform to chloroform/methanol 99:1) to yield 6.8 g (75%) of a white solid after drying. Final purification was achieved by sublimation. m/z=627 ([M+H]+).

Reference： [1]Patent: US2019/140186,2019,A1 .Location in patent: Paragraph 0409-0410

30
[ 908350-80-1 ]
[ 358-23-6 ]
[ 603-35-0 ]
triphenyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-4-yl)phosphonium trifluoromethanesulfonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 14882 - 14886
Angew. Chem.,2019,vol. 131,p. 15024 - 15028,5

31
[ 908350-80-1 ]
2'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[2,4'-bipyridine]-4-carbonitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 14882 - 14886
Angew. Chem.,2019,vol. 131,p. 15024 - 15028,5

32
[ 908350-80-1 ]
C₂₄H₁₅Br₂Cl [ No CAS ]
C₄₆H₃₁ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 18h;Reflux;	A mixture of 5.0 g (10 mmol) of P1, 5.9 g (21 mmol) of <strong>[908350-80-1]2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine</strong> [908350-80-1], 6.4 g (60 mmol) of sodium carbonate, 347 mg (0.3 mmol) of tetrakis(triphenylphosphino)palladium(0), 60 ml of toluene, 15 ml of ethanol and 30 ml of water is heated under reflux with good stirring for 18 h. After cooling, the organic phase is extended with 100 ml of ethyl acetate, removed, washed three times with 50 ml each time of water and once with 100 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The mixture is filtered through a silica gel bed in the form of an ethyl acetate slurry, which is washed through with a little ethyl acetate, the solvent is removed under reduced pressure and the oily residue is recrystallized twice from about 30 ml of acetonitrile with addition of a little ethyl acetate. Yield: 5.2 g (8 mmol), 80%. Purity: about 98% by 1H NMR.

Reference： [1]Patent: US2020/39903,2020,A1 .Location in patent: Paragraph 0175-0176

33
[ 908350-80-1 ]
C₂₄H₁₅BrClI [ No CAS ]
C₃₅H₂₃BrClN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; toluene; for 18h;Reflux;	A mixture of 5.5 g (10 mmol) of P2, 3.1 g (10 mmol) of 2-[4-(4,4,5,5-tetramethyl-1,3.2-dioxaborolan-2-yl)phenyl]pyridine [908350-80-1], 3.2 g (10 mmol) of tetra-n-butylammonium bromide, 2.8 g (20 mmol) of potassium carbonate, 231 mg (0.2 mmol) of tetrakis(triphenylphosphino)palladium(0), 30 ml of toluene and 30 ml of water is heated under reflux with good stirring for 18 h. After cooling, the organic phase is extended with 100 ml of ethyl acetate, removed, washed three times with 50 ml each time of water and once with 100 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The mixture is filtered through a silica gel bed in the form of an ethyl acetate slurry, which is washed through with a little ethyl acetate, the solvent is removed under reduced pressure and the oily residue is recrystallized twice from about 30 ml of acetonitrile with addition of a little ethyl acetate. Yield: 5.2 g (8 mmol), 80%. Purity: about 98% by 1H NMR.

Reference： [1]Patent: US2020/39903,2020,A1 .Location in patent: Paragraph 0180-0181

34
[ 908350-80-1 ]
[ 33301-43-8 ]
C₂₃H₁₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; toluene; at 85℃; for 12h;Inert atmosphere;	III)Take 200mg of compound3 and 300 mg of 2-bromo-1,4-dimethylnaphthalene were added to a 250 mL single-necked bottle with a stirring bar,Add 20mL toluene solution,7mL ethanol solution,7mL water solution,Reflux at 85 for 12h,The reaction is over,filter,The filtrate was extracted with dichloromethane and water.Retain the methylene chloride layer,Add anhydrous Na2SO4 to dry,Evaporate the solvent,Column chromatography gave compound 4 as a white powder.

Reference： [1]Patent: CN110845544,2020,A .Location in patent: Paragraph 0024; 0025; 0026; 0033; 0034

35
[ 5467-74-3 ]
[ 908350-80-1 ]

Reference： [1]Patent: CN110845544,2020,A

36
[ 109-04-6 ]
[ 908350-80-1 ]

Reference： [1]Patent: CN110845544,2020,A

37
[ 1779524-41-2 ]
[ 73183-34-3 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With dimanganese decacarbonyl In acetonitrile at 20℃; for 2h; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Firth, James D.; Hammarback, L. Anders; Burden, Thomas J.; Eastwood, Jonathan B.; Donald, James R.; Horbaczewskyj, Chris S.; McRobie, Matthew T.; Tramaseur, Adam; Clark, Ian P.; Towrie, Michael; Robinson, Alan; Krieger, Jean-Philippe; Lynam, Jason M.; Fairlamb, Ian J. S. [Chemistry - A European Journal, 2021, vol. 27, # 12, p. 3979 - 3985]

38
[ 888041-37-0 ]
[ 908350-80-1 ]
[ 2804043-86-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; toluene for 12h; Reflux;	16 Synthesis of intermediate (29) Intermediate (26) 10.0 g (35.6 mmol), 2,7-dibromotriphenylene 13.7 g (35.6 mmol), Pd(PPh3)4 2.1 g (1.8 mmol), 2 M K2CO3 35.6 mL (210.9 mmol), toluene 178 mL and ethanol 89 mL of the mixture was stirred at reflux for 12 h. After the reaction mixture was cooled to room temperature, the solvent was removed, water was added, the organic layer was separated, dried over anhydrous magnesium sulfate, and the obtained compound was purified by silica gel column chromatography to obtain a yellow solid compound (Intermediate (29) 7.2 g (yield) : 44.0%) was obtained.

Reference： [1]Current Patent Assignee: LAPTO CO LTD - KR2022/30385, 2022, A Location in patent: Paragraph 0610-0613

39
[ 5969-83-5 ]
[ 73183-34-3 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
75.5%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate In 1,4-dioxane at 100℃; for 12h;	14 Synthesis of Intermediate (26) In a one-necked 500 mL flask, 10.0 g (52.7 mmol) of the intermediate (25), 13.4 g (52.7 mmol) of bis(pinacolato)diboron, Pd(dppf)Cl2-CH2Cl2 861 mg (1.1 mol), KOAc 15.5 g (158.2 mmol) and 1,4-dioxane 264 mL were mixed, and then stirred at 100 °C for 12 hours. After the reaction was completed, it was cooled to room temperature, and the reactant was passed through a celite pad and concentrated under reduced pressure. The reaction mixture was purified by silica gel column chromatography (CHCl3) to obtain 11.2 g (yield: 75.5%) of the compound (intermediate (26)) as a white solid.

Reference： [1]Current Patent Assignee: LAPTO CO LTD - KR2022/30385, 2022, A Location in patent: Paragraph 0597; 0598; 0600; 0601

40
[ 51035-40-6 ]
[ 73183-34-3 ]
[ 908350-80-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With bis(cycloocta-1,5-diene)nickel⁽⁰⁾; tripotassium phosphate tribasic; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; tricyclohexylphosphine In 1,4-dioxane at 60℃; for 24h; Inert atmosphere;

Reference： [1]Liu, Xiaojie; Xu, Biping; Su, Weiping [ACS Catalysis, 2022, vol. 12, # 15, p. 8904 - 8910]

41
[ 908350-80-1 ]
[ 2893853-65-9 ]

Yield	Reaction Conditions	Operation in experiment
80 %	Stage #1: 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine With sodium periodate; ammonium acetate In water; acetone at 20℃; Stage #2: In water; acetone at 120℃;

Reference： [1]Kuriyama, Masami; Maeda, Genki; Kamata, Kazuya; Kodama, Yusuke; Yamamoto, Kosuke; Onomura, Osamu [Advanced Synthesis and Catalysis, 2023, vol. 365, # 1, p. 116 - 121]

42
[ 908350-80-1 ]
[ 2803722-87-2 ]

Yield	Reaction Conditions	Operation in experiment
68 %Spectr.	Stage #1: 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine With 2,4,6-trimethyl-pyridine; trifluoromethylsulfonic anhydride; dibenzylamine In ethyl acetate at -78℃; Stage #2: With N-iodo-succinimide In ethyl acetate at 20℃; Stage #3: With ammonium acetate In ethanol; ethyl acetate at 60℃;

Reference： [1]Boyle, Benjamin T.; Levy, Jeffrey N.; de Lescure, Louis; Paton, Robert S.; McNally, Andrew [Science, 2022, vol. 378, # 6621, p. 773 - 779]

43
[ 908350-80-1 ]
[ 105633-27-0 ]
[ 2882831-09-4 ]

Yield	Reaction Conditions	Operation in experiment
41 %	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In ethanol; water; toluene at 95℃; Inert atmosphere;

Reference： [1]Liu, Xinyu; Wu, Meng; Zeng, Ruoqi; Li, Gang; Li, Qiuxia; Li, Feiyang; Yuan, Aihua; Shi, Chao [Inorganic Chemistry, 2022, vol. 61, # 51, p. 20942 - 20948]

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2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.86

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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

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. 908350-80-1 ] {[proInfo.proName]}

Quality Control of [ 908350-80-1 ]

Related Doc. of [ 908350-80-1 ]

Product Details of [ 908350-80-1 ]

Calculated chemistry of [ 908350-80-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 908350-80-1 ]

Application In Synthesis of [ 908350-80-1 ]

[ 908350-80-1 ] Synthesis Path-Upstream 1~2

[ 908350-80-1 ] Synthesis Path-Downstream 1~43

Related Functional Groups of [ 908350-80-1 ]

Organoboron

Aryls

Related Parent Nucleus of [ 908350-80-1 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 908350-80-1 ]

Related Parent Nucleus of
[ 908350-80-1 ]