[ CAS No. 54151-74-5 ] {[proInfo.proName]}

Name: 54151-74-5|2-Bromo-4-phenylpyridine|97%
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SKU: A185231
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Quality Control of [ 54151-74-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54151-74-5 ]

Product Details of [ 54151-74-5 ]

CAS No. :	54151-74-5	MDL No. :	MFCD00235159
Formula :	C₁₁H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KRIILKQTJUOQCJ-UHFFFAOYSA-N
M.W :	234.09	Pubchem ID :	104700
Synonyms :

Calculated chemistry of [ 54151-74-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.37
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.34
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.51
Log Po/w (MLOGP) :	2.82
Log Po/w (SILICOS-IT) :	3.7
Consensus Log Po/w :	3.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.11
Solubility :	0.018 mg/ml ; 0.000077 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.45
Solubility :	0.0823 mg/ml ; 0.000352 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.4
Solubility :	0.00093 mg/ml ; 0.00000397 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 54151-74-5 ]

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 [ 54151-74-5 ]

* 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 [ 54151-74-5 ]
Downstream synthetic route of [ 54151-74-5 ]

[ 54151-74-5 ] Synthesis Path-Upstream 1~9

1
[ 939-23-1 ]
[ 54151-74-5 ]

Yield	Reaction Conditions	Operation in experiment
55.1%	Stage #1: With n-butyllithium; 2-(N,N-dimethylamino)athanol In hexane for 1.5 h; Cooling with ice Stage #2: With carbon tetrabromide In hexane at -78℃; for 0.833333 h;	Dimethylaminoethanol (DMAE, 1.50 mL, 15.0 mmol) was dissolved in hexane (20.0 mL) stirred at ice-cooling. A small amount of n-butyllithium (2.5 mol / L hexane solution, 12.0 mL, 30.0 mmol) was successively dropped under ice-cooling, and the mixture was stirred for 30 minutes. A small amount of 4-phenylpyridine (776 mg, 5.00 mmol) in hexane (30.0 mL) was added dropwise under ice-cooling, and the mixture was stirred for 1 hour in this state.After the reaction solution was cooled to -78 ° C, a small amount of the solution (15.0 mL) of carbon tetrafromide (6.30 g, 18.0 mmol) was successively dropped, and the mixture was stirred for 50 minutes. The purified water was added under ice cooling to stop the reaction, followed by extraction with ethyl acetate (100 mL × 2). The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent to obtain Compound 7 in a yield of 645 mg (yield 55.1percent).

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2028 - 2029
[2] Patent: TW2016/39840, 2016, A, . Location in patent: Paragraph 0020; 0040
[3] Patent: WO2007/20888, 2007, A1, . Location in patent: Page/Page column 43
[4] Journal of the American Chemical Society, 1956, vol. 78, p. 5842

2
[ 58530-53-3 ]
[ 24388-23-6 ]
[ 54151-74-5 ]
[ 98420-98-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile for 24 h; Inert atmosphere; Reflux	General procedure: 2,4-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid pinacol ester (0.11 g, 0.55 mmol), KOH (56 mg, 1.0 mmol), Pd(OAc)₂ (11 mg, 5 mol percent), PPh₃ (52 mg, 20 mol percent) were dissolved in CH₃CN (6 mL). The reaction was stirred at 70 °C under nitrogen atmosphere for 24 h and then cooled. The solid was filtrated off and the filtrate was concentrated. The crude product was then dissolved in CH₂Cl₂ (10 mL) and the solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon evaporation, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give 3w (104 mg, 89percent) as a colorless liquid.

Reference： [1] Tetrahedron, 2013, vol. 69, # 51, p. 10996 - 11003

3
[ 58530-53-3 ]
[ 24388-23-6 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Yield	Reaction Conditions	Operation in experiment
37%	With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 30℃; for 24 h; Inert atmosphere	General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K₂CO₃ (0.14 g, 1.0 mmol), Pd(OAc)₂ (11 mg, 5 mol percent), PPh₃ (26 mg, 10 mol percent) were dissolved in CH₃CN/CH₃OH (2:1, 6 mL). The solution was stirred at 50 °C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH₂Cl₂ (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97percent) as a white solid.

Reference： [1] Tetrahedron, 2013, vol. 69, # 51, p. 10996 - 11003

4
[ 58530-53-3 ]
[ 98-80-6 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 48, p. 11063 - 11072
[2] Tetrahedron, 2006, vol. 62, # 48, p. 11063 - 11072

5
[ 42260-39-9 ]
[ 54151-74-5 ]

Reference： [1] Patent: WO2005/123680, 2005, A1, . Location in patent: Page/Page column 77

6
[ 109-04-6 ]
[ 591-50-4 ]
[ 54151-74-5 ]
[ 32864-29-2 ]

Reference： [1] Organic Letters, 2001, vol. 3, # 6, p. 835 - 838

7
[ 58530-53-3 ]
[ 603-33-8 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 24, p. 5214 - 5228

8
[ 60781-83-1 ]
[ 54151-74-5 ]

Reference： [1] Journal of the American Chemical Society, 1956, vol. 78, p. 5842

9
[ 109-04-6 ]
[ 591-50-4 ]
[ 54151-74-5 ]
[ 32864-29-2 ]

Reference： [1] Organic Letters, 2001, vol. 3, # 6, p. 835 - 838

[ 54151-74-5 ] Synthesis Path-Downstream 1~56

1
[ 60781-83-1 ]
[ 54151-74-5 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5842

2
[ 54151-74-5 ]
[ 92-52-4 ]
[ 6153-92-0 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5842

4
[ 109-04-6 ]
[ 591-50-4 ]
[ 54151-74-5 ]
[ 32864-29-2 ]

Reference： [1]Organic Letters,2001,vol. 3,p. 835 - 838

5
[ 939-23-1 ]
[ 54151-74-5 ]

Yield	Reaction Conditions	Operation in experiment
55.1%		Dimethylaminoethanol (DMAE, 1.50 mL, 15.0 mmol) was dissolved in hexane (20.0 mL) stirred at ice-cooling. A small amount of n-butyllithium (2.5 mol / L hexane solution, 12.0 mL, 30.0 mmol) was successively dropped under ice-cooling, and the mixture was stirred for 30 minutes. A small amount of <strong>[939-23-1]4-phenylpyridin</strong>e (776 mg, 5.00 mmol) in hexane (30.0 mL) was added dropwise under ice-cooling, and the mixture was stirred for 1 hour in this state.After the reaction solution was cooled to -78 C, a small amount of the solution (15.0 mL) of carbon tetrafromide (6.30 g, 18.0 mmol) was successively dropped, and the mixture was stirred for 50 minutes. The purified water was added under ice cooling to stop the reaction, followed by extraction with ethyl acetate (100 mL × 2). The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent to obtain Compound 7 in a yield of 645 mg (yield 55.1%).

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 2028 - 2029
[2]Patent: TW2016/39840,2016,A .Location in patent: Paragraph 0020; 0040
[3]Patent: WO2007/20888,2007,A1 .Location in patent: Page/Page column 43
[4]Journal of the American Chemical Society,1956,vol. 78,p. 5842

6
[ 58530-53-3 ]
[ 98-80-6 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 11063 - 11072
[2]Tetrahedron,2006,vol. 62,p. 11063 - 11072

7
[ 54151-74-5 ]
[ 52565-57-8 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5842

8
[ 42260-39-9 ]
[ 54151-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl bromide; In propiononitrile; at 150℃; for 0.166667h;Microwave;	1B. 4-Phenyl-pyridine-2-carbaldehyde: To a clear, colorless solution of lA (0.850 g, 4.5 mmol) in propionitrile (4.5 mmol) was added trimethylsilyl bromide (2.95 mL, 22.4 mmol). The resulting orange suspension was microwaved in a sealed tube at 150 °C for 10 min. The reaction was cooled to rt and poured into 1.0 N NaOH containing ice. The aqueous layer was extracted with diethyl ether (2x). The combined organic layers were washed with sat. NaHC03, brine, dried over Na2S04, filtered and concentrated to give 1.07 g of 2-bromo-4-phenyl pyridine as an off-white solid. MS 233.9 (M+H) + and 235.9 (M+2+H)+. [00337] To a cooled (-78 °C) clear, slightly yellow solution of 2-bromo-4- phenyl-pyridine (0.500 g, 2.14 mmol) in THF (8.6 mL) was added dropwise 2.5 M n-BuLi in hexane (0.86 mL, 2.14 mmol). The resulting red solution was stirred at-78 °C for 1h, then 1-formylpiperidine (0.48 mL, 4.28 mmol) was added dropwise. The reaction was allowed to warm to 0 °C over 1h and then stirred at 0 °C for 1h. The reaction was quenched with 1.0 N HCl. The reaction was extracted with ethyl acetate. The combined organic layers were washed with sat. NaHC03, brine, dried over Na2S04, filtered, and concentrated to give 0.555 gas a golden oil. Column chromatography (40 g silica gel; gradient elution; 0-40percent ethyl acetate/hexane) provided 1B (0.194 g, 49percent) as a yellow solid. 1H-NMR (400 MHz, CDCI3) No.: 10.16 (s, 1H), 8.84 (d, J = 5.3 Hz, 1H), 8.21 (d, J = 1.3 Hz, 1H), 7.75 (dd, J = 5.3, 1.8 Hz, 1H), 7.71-7.69 (m, 2H), 7.55-7.48 (m, 3H). MS 184.1 (M+H)+.

Reference： [1]Patent: WO2005/123680,2005,A1 .Location in patent: Page/Page column 77

Yield	Reaction Conditions	Operation in experiment
		Besides making 2-bromopyridine, the process of the present invention may be suitable to the preparation of various substituted 2-bromopyridines that could be made by the general Craig procedure. Such substituted 2-bromopyridines would include: 2-bromo-3-picoline 6-bromo-3-picoline 2-bromo-4-picoline 2-bromo-4-ethylpyridine 2-bromo-4-phenylpyridine 2-bromo-2-phenylpyridine 2,5-dibromopyridine
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Inert atmosphere; Reflux;	General procedure: In a 1 L reaction vessel Intermediate A-3 (25 g), Phenylboronic acid (10.74 g), & lt; RTI ID = 0.0 & gt; Pd (PPh3) 4 (3.05 g), K2CO3 (24.3 g) , THF (333 mL) and distilled water (166 mL) were put together, And refluxed under nitrogen for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the aqueous layer was removed. The organic layer was washed with 5% brine (500 mL) And once with distilled water (500 mL). The organic layer obtained was dried over MgSO4, the solvent was removed, and ethyl acetate: n-hexane (= 3: 97) The residue was purified by silica gel column chromatography Purification yielded intermediate A-2 (12.4 g).

10
[ 54151-74-5 ]
[ 57260-71-6 ]
[ 926646-62-0 ]

Reference： [1]Patent: WO2007/20888,2007,A1 .Location in patent: Page/Page column 43-44

11
[ 54151-74-5 ]
[ 98-80-6 ]
[ 26274-35-1 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 7437 - 7443
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 4508 - 4511
Angew. Chem.,2015,vol. 127,p. 4591 - 4594,4

12
[ 54151-74-5 ]
N-[(1E)-6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene]-2-methylpropane-2-sulfinamide [ No CAS ]
N-[(1S)-6-(2-Ethyl-1,3-dioxolan-2-yl)-1-(4-phenylpyridin-2-yl)hexyl]-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (1 eq.) in THF was cooled to -78 C. and treated dropwise with n-BuLi (1.1 eq.). After 30 min, a solution of the imine (O1) (1.2 eq.) in THF was added. The reaction mixture was stirred for 2 h at -78 C. and than slowly warmed to RT. The reaction was quenched with H2O and the aqueous phase was extracted with EtOAc. The combined organic phase was dried (MgSO4) and solvent was removed under reduced pressure. The crude amine was used without further purification

Reference： [1]Patent: US2009/48228,2009,A1 .Location in patent: Page/Page column 68

13
[ 2591-86-8 ]
[ 54151-74-5 ]
[ 55218-76-3 ]

Yield	Reaction Conditions	Operation in experiment
		1B. 4-Phenyl-pyridine-2-carbaldehyde: To a clear, colorless solution of lA (0.850 g, 4.5 mmol) in propionitrile (4.5 mmol) was added trimethylsilyl bromide (2.95 mL, 22.4 mmol). The resulting orange suspension was microwaved in a sealed tube at 150 C for 10 min. The reaction was cooled to rt and poured into 1.0 N NaOH containing ice. The aqueous layer was extracted with diethyl ether (2x). The combined organic layers were washed with sat. NaHC03, brine, dried over Na2S04, filtered and concentrated to give 1.07 g of 2-bromo-4-phenyl pyridine as an off-white solid. MS 233.9 (M+H) + and 235.9 (M+2+H)+. [00337] To a cooled (-78 C) clear, slightly yellow solution of 2-bromo-4- phenyl-pyridine (0.500 g, 2.14 mmol) in THF (8.6 mL) was added dropwise 2.5 M n-BuLi in hexane (0.86 mL, 2.14 mmol). The resulting red solution was stirred at-78 C for 1h, then 1-formylpiperidine (0.48 mL, 4.28 mmol) was added dropwise. The reaction was allowed to warm to 0 C over 1h and then stirred at 0 C for 1h. The reaction was quenched with 1.0 N HCl. The reaction was extracted with ethyl acetate. The combined organic layers were washed with sat. NaHC03, brine, dried over Na2S04, filtered, and concentrated to give 0.555 gas a golden oil. Column chromatography (40 g silica gel; gradient elution; 0-40% ethyl acetate/hexane) provided 1B (0.194 g, 49%) as a yellow solid. ¹H-NMR (400 MHz, CDCI3) No.: 10.16 (s, 1H), 8.84 (d, J = 5.3 Hz, 1H), 8.21 (d, J = 1.3 Hz, 1H), 7.75 (dd, J = 5.3, 1.8 Hz, 1H), 7.71-7.69 (m, 2H), 7.55-7.48 (m, 3H). MS 184.1 (M+H)+.

Reference： [1]Patent: WO2005/123680,2005,A1 .Location in patent: Page/Page column 77

14
[ 504-29-0 ]
[ 54151-74-5 ]
[ 1238944-73-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 90℃; for 17h;Inert atmosphere;	(4-Phenyl-pyridin-2-yl)-pyridin-2-yl-amine (I) 2-Bromo-4-phenylpyridine (280 mg, 1.19 mmol), 2-aminopyridine (124 mg, 1.31 mmol), potassium terf-butoxide (201 mg, 1.79 mmol), (+/-)-BINAP (3 mg, 0.05 mmol) and Pd2(dba)3 (2.7 mg, 0.03 mmol) were stirred in toluene (2.5 ml_) at 9O0C under Ar(g). After 17h stirring, the reaction mixture was diluted with CH2CI2 (2.5 mL) and silica was added. The solvent was removed under reduced pressure and the resulting dry loaded material purified by silica gel column chromatography, eluting with CH2CI2/Me0H (100:2), to furnish I as a yellow solid (183 mg, 62%).1H NMR (400MHz, CDCI3) δH: 8.29 (t, J=5.8Hz, 2H), 7.91-7.78 (m, 1H), 7.72- 7.58 (m, 4H), 7.54-7.39 (m, 3H), 7.12 (d, J=4.5Hz, 1 H), 6.94-6.85 (m, 1 H). MW: 247.29 LCMS (ES): found 248.1. [MH]+.

Reference： [1]Patent: WO2010/86646,2010,A1 .Location in patent: Page/Page column 34

15
[ 54151-74-5 ]
[ 1418754-19-4 ]
C₂₉H₃₃N₅*2C₂HF₃O₂ [ No CAS ]

Reference： [1]Patent: WO2013/12827,2013,A1 .Location in patent: Paragraph 00403

16
[ 54151-74-5 ]
[ 1451007-58-1 ]
[ 1451006-92-0 ]

Yield	Reaction Conditions	Operation in experiment
6%		Example 65 (S)-2-(tert-Butoxy)-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-(4-phenylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acid To a solution of (S)-methyl 2-(2-bromo-7-(4,4-dimethylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.050 g, 0.107 mmol, 1 equiv) in dioxane (1.0 mL) was added <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (0.030 g, 0.128 mmol, 1.2 equiv), hexabutyldistannane (0.12 mL, 0.235 mmol, 2.2 equiv), and Pd(PPh3)4 (0.012 g, 0.011 mmol, 0.1 equiv). The reaction was heated at 85 C. for 72 h. The reaction temperature was then lowered to 60 C. Methanol (1 mL), water (0.3 mL), and LiOH.H2O (26 mg, 1.07 mmol, 10 equiv) added and heating was continued for 2 h. Upon completion of the saponification, the reaction was removed from heat and filtered through a syringe filter. The crude reaction mixture was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19200 mm, 5-μm particles; Guard Column. Waters XBridge C18, 1910 mm, 5-μm particles; Mobile Phase A: water with 20-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 20-mM ammonium acetate; Gradient: 45-85% B over 20 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min, to provide (S)-2-(tert-butoxy)-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-(4-phenylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (3.5 mg, 6%). 1H NMR (500 MHz, DMSO-d6) δ 8.73 (d, J=4.9 Hz, 1H), 8.48 (s, 1H), 7.83 (d, J=7.6 Hz, 2H), 7.75 (d, J=4.0 Hz, 1H), 7.60-7.49 (m, 3H), 7.06 (s, 1H), 5.72 (br. s., 1H), 3.61-3.55 (m, 4H), 2.53 (s, 3H), 1.65 (br. s., 2H), 1.50 (br. s., 2H), 1.18 (s, 9H), 1.11 (br. s., 6H). LCMS (ESI, M+1): 528.3.

Reference： [1]Patent: US2013/231331,2013,A1 .Location in patent: Paragraph 0244-0245

17
[ 58530-53-3 ]
[ 24388-23-6 ]
[ 54151-74-5 ]
[ 98420-98-5 ]

Yield	Reaction Conditions	Operation in experiment
6%; 89%	With palladium diacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; for 24h;Inert atmosphere; Reflux;	General procedure: <strong>[58530-53-3]2,4-dibromopyridine</strong> (0.12 g, 0.50 mmol), phenylboronic acid pinacol ester (0.11 g, 0.55 mmol), KOH (56 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (52 mg, 20 mol %) were dissolved in CH3CN (6 mL). The reaction was stirred at 70 C under nitrogen atmosphere for 24 h and then cooled. The solid was filtrated off and the filtrate was concentrated. The crude product was then dissolved in CH2Cl2 (10 mL) and the solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon evaporation, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give 3w (104 mg, 89%) as a colorless liquid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10996 - 11003

18
[ 58530-53-3 ]
[ 24388-23-6 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Yield	Reaction Conditions	Operation in experiment
13%; 9%; 37%	With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 30℃; for 24h;Inert atmosphere;	General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10996 - 11003

19
[ 58530-53-3 ]
[ 603-33-8 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 5214 - 5228

20
[ 54151-74-5 ]
[ 98-80-6 ]
methyl 6-oxo-2-phenyl-6H-pyrido[2,1-a]isoquinoline-7-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 4508 - 4511
Angew. Chem.,2015,vol. 127,p. 4591 - 4594,4

21
[ 54151-74-5 ]
[ 5720-05-8 ]
4-phenyl-2-(p-tolyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6087 - 6092

22
[ 54151-74-5 ]
[ 5720-05-8 ]
N-(5-methyl-2-(4-phenylpyridin-2-yl)phenyl)acetamide [ No CAS ]
2-(2-isocyanato-4-methylphenyl)-4-phenylpyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6087 - 6092

23
[ 54151-74-5 ]
[ 1679-18-1 ]
2-(4-chlorophenyl)-4-phenylpyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6087 - 6092

24
[ 54151-74-5 ]
[ 3638-73-1 ]
7-bromo-3-phenylbenzo[4,5]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.80%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h;Reflux;	Compound 7 (645 mg, 2.75 mmol) was dissolved in xylene (30.0 mL) Copper iodide (I) (105 mg, 0.550 mmol), cesium carbonate (2.67 g, 8.26 mmol) and 1,10-phenanthroline (198 mg, 1.10 mmol) were added to a solution of 4-dibromoaniline (690 mg, 2.75 mmol) And the mixture was heated under reflux for 24 hours with stirring. The reaction solution was returned to room temperature and extracted with ethyl acetate (100 mL × 2). The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent to obtain Compound 8 in a yield of 78.4 mg (yield 8.80%)

Reference： [1]Patent: TW2016/39840,2016,A .Location in patent: Paragraph 0020; 0041

25
[ 54151-74-5 ]
7-iodo-3-phenylbenzo[4,5]imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Patent: TW2016/39840,2016,A

26
[ 54151-74-5 ]
3-phenyl-7-(tributylstannyl)benzo[4,5]imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Patent: TW2016/39840,2016,A

27
[ 54151-74-5 ]
[ 939-23-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With methanol; magnesium; at 20℃;	General procedure: The aryl halide was dissolved in 5mL of methanol per mmol of (hetero)arylhalide, magnesium (5 equiv.) added and the mixture was stirred at room temperature. After completion of the reaction (between 6-12h), the reaction mixture was poured into water, acidified with dilute HCl, and extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The product was purified if necessary by column chromatography on silica gel.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 3108 - 3111

28
[ 54151-74-5 ]
3,5‐bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenol [ No CAS ]
C₂₈H₂₀N₂O [ No CAS ]

Reference： [1]Patent: US2018/212158,2018,A1 .Location in patent: Paragraph 0568

29
[ 54151-74-5 ]
2-(5-bromo-[1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
2-(5-bromo-[1,1′-biphenyl]-3-yl)-4-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; ethanol; water; for 17h;Reflux;	5 grams (g) (17.9 millimoles, mmol, 1.2 equivalents, equiv.) of Intermediate A, 3.5 g (14.9 mmol, 1 equiv.) of <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong>, 1.2 g (1.05 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 5.2 g (37.4 mmol, 2.5 equiv.) of potassium carbonate were mixed with 50 milliliters (mL) (concentration 0.6 molar, M) of a solvent in which tetrahydrofuran (THF), distilled water (H2O), and ethanol (EtOH) were mixed at a ratio of 3:1:1, and the mixture was refluxed for 17 hours. The resultant mixture was cooled to room temperature and a precipitate was filtered. Then, a filtrate obtained therefrom was washed by using ethyl acetate (EA)/H2O and purified by column chromatography (while increasing a rate of MC/Hex to between 25% and 50%) to obtain 4.2 g (yield: 72%) of Intermediate B. The obtained product was confirmed by Mass Spectrometry and HPLC analysis.HRMS (MALDI) calcd for C23H16BrN: m/z 385.0466, Found: 385.0465.

Reference： [1]Patent: US2018/305386,2018,A1 .Location in patent: Paragraph 0313; 0314; 0315

30
[ 54151-74-5 ]
(4-phenyl-2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-3-yl)pyridine) [ No CAS ]

Reference： [1]Patent: US2018/305386,2018,A1

31
[ 54151-74-5 ]
3,6-di-tert-butyl-1-(1-phenyl-4-(5-(4-phenylpyridin-2-yl)-[1,1′-biphenyl]-3-yl)-1H-benzo[d]imidazol-2-yl)-9H-carbazole [ No CAS ]

Reference： [1]Patent: US2018/305386,2018,A1

32
[ 54151-74-5 ]
[ 244205-40-1 ]
C₁₇H₁₂BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 18h;Reflux;	4.00 g (17.1 mmol, 1.0 equiv.) of Intermediate b1, 4.12 g (20.51 mmol, 1.2 equiv.) of (2-bromophenyl)boronic acid, 1.38 g (1.20 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 4.53 g (42.72 mmol, 2.5 equiv.) of sodium carbonate were mixed with a solvent (0.6 M) in which toluene, ethanol, and distilled water (H2O) were mixed at a ratio of 3:1:1, and the resulting mixture was refluxed for 18 hours. The mixture obtained therefrom was cooled to room temperature, and a precipitate was filtered therefrom to obtain a solid. The obtained solid was washed with EA/H2O and purified by column chromatography (while increasing a rate of EA/Hex to between 5% and 10%) to obtain 4.24 g (yield: 80%) of Intermediate B1. The obtained product was identified by Mass and HPLC analysis. HRMS (MALDI) calcd for C17H12BrN: m/z 309.0153, Found: 309.0154.

Reference： [1]Patent: US2018/342686,2018,A1 .Location in patent: Paragraph 0321; 0325-0327

33
[ 54151-74-5 ]
C₄₀H₂₉N₃ [ No CAS ]

Reference： [1]Patent: US2018/342686,2018,A1

34
[ 54151-74-5 ]
C₄₀H₂₇N₃Pt [ No CAS ]

Reference： [1]Patent: US2018/342686,2018,A1

35
[ 54151-74-5 ]
(4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine) [ No CAS ]

Reference： [1]Patent: US2019/6608,2019,A1
[2]Patent: US2019/58144,2019,A1
[3]Patent: US2019/165292,2019,A1

36
[ 54151-74-5 ]
(2,4-di-tert-butyl-6-(1-phenyl-4-(3-(4-phenylpyridin-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)phenol) [ No CAS ]

Reference： [1]Patent: US2019/6608,2019,A1
[2]Patent: US2019/58144,2019,A1
[3]Patent: US2019/165292,2019,A1

37
[ 54151-74-5 ]
[ 89598-96-9 ]
(2-(3-bromophenyl)-4-phenylpyridine) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 12h;Reflux;	3 grams (g) (13 millimoles, mmol) of 2-bromo-4- phenylpyridine, 3.1 g (1.2 equivalents, equiv.) of (3-bro- mophenyl)boronic acid, 1.1 g (0.9 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.4 g (32 mmol, 3 equiv.) of sodium carbonate were mixed with 49 milliliters (mE) of a solvent in which tetrahydrofuran (THF) and distilled water (H20) were mixed at a volume ratio of 3:1, and then refluxed for 12 hours. A reaction product obtained therefrom was cooled to room temperature, and a precipitate was filtered therefrom to obtain a filtrate. Then, the filtrate was washed by using ethyl acetate (EA)/H20, and purified by column chromatography (while increasing a rate of MC (methylene chloride)/Hex (hexane) to between 25% and 50%) to obtain 3.2 g (yield: 80%) of Intermediate A. The obtained compound was identified by mass spectrometry and HPEC analysis. HRMS (MALDI) calcd for C17H12BrN: mlz 309.0153, Found: 309.0155.
80%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 12h;Reflux;	3 grams (g) (13 millimoles, mmol) of <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong>, 3.1 g (1.2 equivalents, equiv.) of (3-bromophenyl)boronic acid, 1.1 g (0.9 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.4 g (32 mmol, 3 equiv.) of sodium carbonate were mixed with 49 milliliters (mL) (0.6 molar, M) of a solvent in which tetrahydrofuran (THF) and distilled water (H2O) were mixed at a volume ratio of 3:1, The reaction mixture was then refluxed for 12 hours. The reaction product obtained therefrom was cooled to room temperature, and the precipitate was filtered to obtain a filtrate. The filtrate was washed with ethyl acetate (EA)/H2O, and the crude product was purified by column chromatography (while increasing a rate of MC(methylene chloride)/Hex(hexane) to between 25% and 50%) to obtain 3.2 g (yield: 80%) of Intermediate A. The obtained compound was identified by mass spectroscopy and HPLC analysis. (0411) HRMS (MALDI) calcd for C17H12BrN: m/z 309.0153, Found: 309.0155.
80%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 12h;Reflux;	3 grams (g) (13 millimoles (mmol)) of <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong>, 3.1 g (1.2 equivalents (equiv.)) of (3-bromophenyl)boronic acid, 1.1 g (0.9 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.4 g (32 mmol, 3 equiv.) of sodium carbonate were mixed with 49 milliliters (mL) of a solvent (0.6 molar (M)) in which tetrahydrofuran (THF) and distilled water (H2O) were mixed at a ratio of 3:1, and then refluxed for 12 hours. The resultant mixture was cooled to room temperature, and a precipitate was filtered. The filtrate obtained therefrom was washed by using ethyl acetate (EA) and H2O and purified by column chromatography (while increasing a rate of MC/Hex to between 25% to 50%) to obtain 3.2 g (yield: 80%) of Intermediate A. The obtained product was identified by Mass and HPLC analysis. HRMS (MALDI) calcd for C17H12BrN: m/z 309.0153, Found: 309.0155.

Reference： [1]Patent: US2019/6608,2019,A1 .Location in patent: Paragraph 0362; 0363; 0364; 0365
[2]Patent: US2019/58144,2019,A1 .Location in patent: Paragraph 0409-0411
[3]Patent: US2019/165292,2019,A1 .Location in patent: Paragraph 0394; 0395; 0396

38
[ 54151-74-5 ]
(±)-trans-1,3-isopropyl 3-(4-(5-(aminomethyl)-1-methyl-1H-1,2,3-triazol-4-yl)phenoxy)cyclohexane-1-carboxylate [ No CAS ]
(±)-trans-3-(4-(1-methyl-5-(((4-phenylpyridin-2-yl)amino)methyl)-1H-1,2,3-triazol-4-yl)phenoxy)cyclohexanecarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%		mixture of Intermediate 4 (8 mg, 0.021 mmol), <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (8 mg, 0.032 mmol), BINAP (5 mg, 8.6 pmol), Pd(dba)2 (2 mg, 4.3 pmol) and Cs2C03 (21 mg, 0.064 mmol) in toluene (0.5 mL) was degassed with Ar for 5 min. and then heated to H0C overnight. LC/MS indicated the formation of the desired product. The reaction was cooled to RT and concentrated in vacuo. To the crude product was added THF (0.8 mL), water (0.4 mL), MeOH (0.4 mL) and LiOH.LhO (7 mg, 0.168 mmol) at RT, after which the reaction was stirred at RT overnight, then was concentrated in vacuo. The residue was dissolved in H20 (5 mL), and the pH was adjusted with 1N aq. HC1 to ~3 and extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by preparative LC/MS (Column: Waters XBridge C18, 19 x 200 mm, 5-pm particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 50-90% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min) to give the title compound (1.0 mg, 2.1 pmol, 10% yield). LCMS, [M + H]+ = 484.1. NMR (500 MHz, DMSO-d6) d 8.04 (d, J=5.5 Hz, 1H), 7.64 - 7.55 (m, 4H), 7.48 - 7.38 (m, 3H), 7.00 (d, =8.9 Hz, 2H), 6.94 (d, J=5.5 Hz, 1H), 6.80 (s, 1H), 4.70 (br. s., 2H), 4.66 - 4.60 (m, 1H), 4.05 (s, 3H), 2.66 - 2.55 (m, 1H), 1.94 - 1.39 (m, 8H).

Reference： [1]Patent: WO2019/126093,2019,A1 .Location in patent: Page/Page column 144

39
[ 557-21-1 ]
[ 54151-74-5 ]
4-phenylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.48 g	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl acetamide; at 120℃;Inert atmosphere;	A solution of 2-bromo-4- phenylpyridine (14’, 0.5 g, 2.1 mmol), zinc cyanide (0.3 g, 2.6 mmol) and Pd(PPh3)4 (0.25 g, 0.22 mmol) in DMA (5 mL) was evacuated and back filled with nitrogen (3x), placed under N:? atmosphere and allowed to stir at 120 C overnight. A mixture of 2-cyano-4-phenylpyridine and 4-phenylpicolinamide (15’) was obtained (0.48 g) and therefore it was decided to convert the mixture to the acid and isolate the acid. MS m/e: 199 (M+H)•.

Reference： [1]Patent: WO2019/231942,2019,A1 .Location in patent: Paragraph 0166

40
[ 54151-74-5 ]
N-(5-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)pyridin-2-yl)-4-phenylpicolinamide [ No CAS ]

Reference： [1]Patent: WO2019/231942,2019,A1

41
[ 54151-74-5 ]
[ 52565-56-7 ]

Reference： [1]Patent: WO2019/231942,2019,A1

42
[ 14368-40-2 ]
[ 54151-74-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5458 - 5465
[2]Patent: KR2021/91537,2021,A

43
C₁₃H₁₄N₂ [ No CAS ]
[ 54151-74-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With Acetyl bromide; water; In ethyl acetate; at 0 - 20℃; for 4h;	General procedure: AcBr (13.0) as an acetyl halogen compound in a solution of 0.65 mmol (1.0 equiv) of the enamine compound (alkylidene nitrile, compound 3) in ethyl acetate (EA, 1.3 mL) and H2O (0.4 mL) mmol, 20.0 equiv) or AcCl (13.0 mmol, 20.0 equiv) were slowly added dropwise in an ice bath at 0C.The ice bath was removed and the resulting mixture was warmed to room temperature and stirred for 4 hours. After the reaction was completed by monitoring by TLC, itwas quenched with a saturated aqueous solution ofNaHCO3.After separation of the organic layer, the resulting mixture was extracted with ethyl acetate, and the mixed organic phase was dried over anhydrous MgSO4.After filtration and evaporation of the solvent, the crude residue was purified by silica gel chromatography (Kieselgel 60 F254 plate, Merk; 4-10% ethyl acetate in hexane) to 4-aryl-2-halo of Examples 1 to 20. A pyridine derivative (Compound 1) was obtained.

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5458 - 5465
[2]Patent: KR2021/91537,2021,A .Location in patent: Paragraph 0069-0072; 0078-0079; 0084-0086

44
[ 54151-74-5 ]
7-bromo-9H-pyrido[2,3-b]indole [ No CAS ]
C₂₂H₁₄BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate; In toluene; for 168h;Reflux; Inert atmosphere;	Starting material 3-A (9.9 g, 40 mmol), starting material 3-B (18.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.1 g, 80 mmol), and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring at a nitrogen atmosphere for 7 days. The reaction mixture was cooled to room temperature, and 300 ml of water was added to isolate the organic layer. The water layer was extracted twice with 250 ml of dichloromethane to obtain an organic layer. The extracted organic layer was stirred with MgSO4 to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The resulting solid was subjected to column chromatography using, as an eluent, dichloromethane and normal hexane to obtain 4.3 g of Intermediate 3-C at the yield of 27%. MS (MALDI-TOF) m/z: 400 [M]+

Reference： [1]Patent: US2020/99001,2020,A1 .Location in patent: Paragraph 0510-0512

45
[ 54151-74-5 ]
C₄₆H₂₆N₆Pt [ No CAS ]

Reference： [1]Patent: US2020/99001,2020,A1

46
[ 54151-74-5 ]
C₁₁H₁₂BN₃O₄ [ No CAS ]
6-methyl-8-(4-phenylpyridin-2-yl)benzo[e][1,2,4]triazine-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; water; toluene; at 120℃; for 0.5h;Inert atmosphere;	The crude product of compound 4-1 (100mg) and compound 7-1 (90mg, 0.43mmol) were dissolved in toluene (21mL) and ethanol (7mL) under strict nitrogen protection, and [1,1'-bis(diphenylphosphino) was added Ferrocene] Palladium dichloride (15mg, 0.02mmol) and sodium carbonate aqueous solution (2M, 0.47mL), heated to 120C and refluxed for 30min. TLC monitors the reaction. After the reaction of compound 7-1, it was cooled to room temperature, and EA/H2O was added for liquid separation. The organic phase was dried with anhydrous sodium sulfate, concentrated, and eluted with silica gel column chromatography with PE/EA=4/1-2/1 to obtain the compound 7 Crude product (80 mg), pale yellow solid. After beating a small amount of ether, 10 mg of pure product was obtained as a white solid, and the yield was 20%.

Reference： [1]Patent: CN111440146,2020,A .Location in patent: Paragraph 0097-0100

47
[ 6165-68-0 ]
[ 54151-74-5 ]
4-phenyl-2-(thiophene-2-yl)pyridine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 4384 - 4390

48
[ 54151-74-5 ]
rel-(2aS,2a¹S,3S,3aR,6aR)-6a-methyl-3-(2-(4-phenylpyridin-2-yl)thiophen-3-yl)-2,2a,2a¹,3,3a,6a-hexahydro-4H-cyclobuta[cd]benzofuran-4-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 4384 - 4390

49
[ 54151-74-5 ]
C₁₈H₁₈BClO₃ [ No CAS ]
C₂₃H₁₄ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 120℃; for 12h;	100 mmol of 2-bromopyridine-4-phenyl, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh3)4 was added.React at 120C for 12h.After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, filtered and washed with water, and the obtained solid was recrystallized and purified with toluene to obtain a white powder M4.Wherein,the added amount ofPd(PPh3)4is 1 mol% of M3.

Reference： [1]Patent: CN113024512,2021,A .Location in patent: Paragraph 0116-0119; 0123

50
[ 58530-53-3 ]
[ 100-58-3 ]
[ 54151-74-5 ]
[ 26274-35-1 ]
[ 98420-98-5 ]

Reference： [1]Journal of the American Chemical Society,2021,vol. 143,p. 9682 - 9693

51
[ 54151-74-5 ]
[ 4612-26-4 ]
C₂₈H₂₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 24h;Inert atmosphere; Resolution of racemate;	(i) Combine 1,4-biphenylboronic acid (1.04g, 6.30mmol) and <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (4.42g, 18.9mmol), K2CO3 (1.80g, 13.0mmol), tetrakis(triphenyl) Phosphine) Palladium (1.31g, 1.13mmol) dissolvedIn 1,4-dioxane (50.0 mL). The mixture was refluxed under N2 for 24 hours. After the reaction mixture was cooled to room temperature and all solvents were removed by rotary evaporation, it was extracted with dichloromethane, washed with water, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by silica gel column chromatography to obtain compound III as a white solid.

Reference： [1]Journal of Materials Chemistry C,2021,vol. 9,p. 9505 - 9514
[2]Patent: CN113336800,2021,A .Location in patent: Paragraph 0108-0114

52
[ 54151-74-5 ]
(8-cyclohexyl-5-hydroxy-1-(4-phenylpyridin-2-yl)-9,10-dihydrophenanthren-9-yl)methyl acetate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2022,vol. 228

53
[ 54151-74-5 ]
(8-(4-bromophenyl)-5-hydroxy-1-(4-phenylpyridin-2-yl)-9,10-dihydrophenanthren-9-yl)methyl acetate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2022,vol. 228

54
[ 54151-74-5 ]
1-(4-bromophenyl)-10-(hydroxymethyl)-8-(4-phenylpyridin-2-yl)-9,10-dihydrophenanthren-4-ol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2022,vol. 228

55
[ 54151-74-5 ]
C₄₉H₄₉BN₂O₃ [ No CAS ]
C₅₄H₄₅N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In ethanol; water monomer; toluene; for 10h;Inert atmosphere; Reflux;	12.0 mmol of Int-11 was dissolved in 60 mL of toluene, under nitrogen protection, 10.0 mmol of <strong>[54151-74-5]4-phenyl-2-bromopyridine</strong> (reactant 5) was added,36.0 mmol of anhydrous potassium carbonate, 0.1 mmol of Pd132 catalyst, 30.0 mL of ethanol and 30.0 mL of water were heated and refluxed and stirred for 10 hours, Cool to room temperature, add 100 mL of saturated brine solution, extract with dichloromethane, collect the organic phase, dry, filter, concentrate the filtrate to dryness under reduced pressure, and separate and purify with a silica gel column.The compound CJH74 was obtained as a yellow solid with a yield of 78%.

Reference： [1]Patent: CN113735853,2022,B .Location in patent: Paragraph 0167; 0182-0183

56
[ 54151-74-5 ]
3-(pyridin-2-yl)-1,2-thiazol-5-amine [ No CAS ]
4-phenyl-N-[3-(pyridin-2-yl)-1,2-thiazol-5-yl]pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 16h;Inert atmosphere; Sealed tube;	CS2CO3 (519.30 mg, 1.60 mmol) was added to a stirred solution of 3-(pyridin-2-yl)-l,2-thiazol-5-amine (150 mg, 0.64 mmol) and <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (90.5 mg, 0.51 mmol) in toluene (5 mL), and the reaction mixture was degassed with argon for 10 min. Pd2(dba)3 (58.53 mg. 0.06 mmol) and BINAP (79.59 mg, 0.13 mmol) were added and the resulting mixture was heated at 100 C for 16 h in a sealed tube. After completion, the reaction mixture was filtered through a short pad of celite. The filtrate was diluted with water and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified to afford 4-phenyl-N-[3-(pyridin-2-yl)- l,2-thiazol-5-yl]pyridin-2-amine (30 mg, 14%). MS (ESI): m/z 331.0 [M+l]+.

Reference： [1]Patent: WO2022/87326,2022,A1 .Location in patent: Paragraph 00442

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[ 50488-34-1 ]

2-Bromo-4-(tert-butyl)pyridine

Similarity: 0.87

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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. 54151-74-5 ] {[proInfo.proName]}

Quality Control of [ 54151-74-5 ]

Related Doc. of [ 54151-74-5 ]

Product Details of [ 54151-74-5 ]

Calculated chemistry of [ 54151-74-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 54151-74-5 ]

Application In Synthesis of [ 54151-74-5 ]

[ 54151-74-5 ] Synthesis Path-Upstream 1~9

[ 54151-74-5 ] Synthesis Path-Downstream 1~56

Related Functional Groups of [ 54151-74-5 ]

Aryls

Bromides

Related Parent Nucleus of [ 54151-74-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 54151-74-5 ]

Related Parent Nucleus of
[ 54151-74-5 ]