[ CAS No. 142137-17-5 ] {[proInfo.proName]}

Name: 142137-17-5|3-Bromo-5-phenylpyridine|98%
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Quality Control of [ 142137-17-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 142137-17-5 ]

SDS Specification

Alternatived Products of [ 142137-17-5 ]

Product Details of [ 142137-17-5 ]

CAS No. :	142137-17-5	MDL No. :	MFCD04114223
Formula :	C₁₁H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AWCQJXPOCRXHNK-UHFFFAOYSA-N
M.W :	234.09	Pubchem ID :	2762904
Synonyms :

Calculated chemistry of [ 142137-17-5 ]

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) :	-5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.35
Log Po/w (XLOGP3) :	3.17
Log Po/w (WLOGP) :	3.51
Log Po/w (MLOGP) :	2.82
Log Po/w (SILICOS-IT) :	3.7
Consensus Log Po/w :	3.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.91
Solubility :	0.0291 mg/ml ; 0.000124 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.181 mg/ml ; 0.000774 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 :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 142137-17-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 142137-17-5 ]

* 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 [ 142137-17-5 ]
Downstream synthetic route of [ 142137-17-5 ]

[ 142137-17-5 ] Synthesis Path-Upstream 1~9

1
[ 625-92-3 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate In 1,2-dimethoxyethane; waterHeating / reflux	A mixture of 3,5-dibromopyridine (10.0 g, 42.2 mmol), phenylboronic acid (4.6 g, 38.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.25 mmol), potassium carbonate (17.5 g, 127 mmol), water (63 ml) and 1,2-dimethoxyethane (126 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (1 M, 60 ml) was added followed by extraction twice with diethyl ether (100 ml). Chromatography on silica gel with dichloromethane as solvent gave the title compound. Yield 6.1 g, 68percent, Mp 42-44° C.
68%	With potassium carbonate In 1,2-dimethoxyethane; water	A mixture of 3,5-dibromopyridine (10.0 g, 42.2 mmol), phenylboronic acid (4.6 g, 38.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.25 mmol), potassium carbonate (17.5 g, 127 mmol), water (63 ml) and 1,2-dimethoxyethane (126 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (1 M, 60 ml) was added followed by extraction twice with diethyl ether (100 ml). Chromatography on silica gel with dichloromethane as solvent gave the title compound. Yield 6.1 g, 68percent, Mp 42-44 C.
68%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 4 h; Reflux	(Triphenylphosphine)palladium tetrakis (125 mg, 0.08 mmol, 2 mol percent) was added to a solution of3,5-dibromopyridine (1.00 g, 4.22 mmol) in dimethoxyethane (13 mL) and themixture was stirred for 10 min. Asolution of potassium carbonate (1.75 g, 12.7 mmol) in water (6.5 mL) wasadded, followed by phenyl boronic acid (463 mg, 3.79 mmol), and the mixture washeated at reflux for 4 h. A solution of1M NaOH (6 mL) was added to the cooled mixture, the mixture was extracted withdiethyl ether, the organic extracts were combined, dried over MgSO₄, filtered, and the solvents were evaporated. The crude was purified by columnchromatography using dichloromethane as an eluent to give 608 mg of the product(68 percent yield) as a white solid. ¹HNMR (CDCl₃, 300 MHz): δ 8.76(d, 1H, 2.0 Hz); 8.66 (d, 1H, 2.2 Hz); 8.03 (t, 1H, 2.2 Hz, 2.0 Hz); 7.43-7.59(m, 5H). ¹³CNMR(CDCl₃, 75 MHz): δ 149.3,146.3, 138.2, 136.8, 136.2, 129.1, 128.6, 127.1, 120.8,

Reference： [1] Journal of Materials Chemistry C, 2014, vol. 2, # 47, p. 10129 - 10137
[2] Patent: US2004/72823, 2004, A1, . Location in patent: Page/Page column 20
[3] Patent: US2004/72823, 2004, A1, . Location in patent: Page/Page column 15
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4145 - 4149
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5820 - 5825
[6] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2217 - 2226
[7] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 17, p. 2825 - 2828
[8] Patent: US5861423, 1999, A,
[9] Patent: US5811442, 1998, A,
[10] Patent: WO2008/91681, 2008, A2, . Location in patent: Page/Page column 240-241
[11] Patent: WO2009/10530, 2009, A1, . Location in patent: Page/Page column 87
[12] Patent: US2010/16298, 2010, A1, . Location in patent: Page/Page column 203

2
[ 625-92-3 ]
[ 110-71-4 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Reference： [1] Patent: US2003/4153, 2003, A1,
[2] Patent: US6392045, 2002, B1,

3
[ 625-92-3 ]
[ 591-50-4 ]
[ 142137-17-5 ]

Reference： [1] Synlett, 2002, # 6, p. 1008 - 1010

4
[ 625-92-3 ]
[ 497-19-8 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Reference： [1] Patent: US5409920, 1995, A,

5
[ 625-92-3 ]
[ 603-33-8 ]
[ 142137-17-5 ]

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

6
[ 625-92-3 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Reference： [1] Patent: US5733912, 1998, A,

7
[ 13535-01-8 ]
[ 591-50-4 ]
[ 73183-34-3 ]
[ 142137-17-5 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933

8
[ 142137-17-5 ]
[ 850991-38-7 ]

Reference： [1] Patent: WO2008/91681, 2008, A2, . Location in patent: Page/Page column 241
[2] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673

9
[ 5419-55-6 ]
[ 142137-17-5 ]
[ 850991-38-7 ]

Reference： [1] Patent: US2010/16298, 2010, A1, . Location in patent: Page/Page column 203-204

[ 142137-17-5 ] Synthesis Path-Downstream 1~59

1
[ 505-66-8 ]
[ 142137-17-5 ]
1-(5-phenyl-pyridin-3-yl)-homopiperazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2217 - 2226

2
[ 625-92-3 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water;Heating / reflux;	A mixture of 3,5-dibromopyridine (10.0 g, 42.2 mmol), phenylboronic acid (4.6 g, 38.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.25 mmol), potassium carbonate (17.5 g, 127 mmol), water (63 ml) and 1,2-dimethoxyethane (126 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (1 M, 60 ml) was added followed by extraction twice with diethyl ether (100 ml). Chromatography on silica gel with dichloromethane as solvent gave the title compound. Yield 6.1 g, 68%, Mp 42-44 C.
68%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water;	A mixture of 3,5-dibromopyridine (10.0 g, 42.2 mmol), phenylboronic acid (4.6 g, 38.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.25 mmol), potassium carbonate (17.5 g, 127 mmol), water (63 ml) and 1,2-dimethoxyethane (126 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (1 M, 60 ml) was added followed by extraction twice with diethyl ether (100 ml). Chromatography on silica gel with dichloromethane as solvent gave the title compound. Yield 6.1 g, 68%, Mp 42-44 C.
68%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; for 4h;Reflux;	(Triphenylphosphine)palladium tetrakis (125 mg, 0.08 mmol, 2 mol %) was added to a solution of3,5-dibromopyridine (1.00 g, 4.22 mmol) in dimethoxyethane (13 mL) and themixture was stirred for 10 min. Asolution of potassium carbonate (1.75 g, 12.7 mmol) in water (6.5 mL) wasadded, followed by phenyl boronic acid (463 mg, 3.79 mmol), and the mixture washeated at reflux for 4 h. A solution of1M NaOH (6 mL) was added to the cooled mixture, the mixture was extracted withdiethyl ether, the organic extracts were combined, dried over MgSO4, filtered, and the solvents were evaporated. The crude was purified by columnchromatography using dichloromethane as an eluent to give 608 mg of the product(68 % yield) as a white solid. 1HNMR (CDCl3, 300 MHz): δ 8.76(d, 1H, 2.0 Hz); 8.66 (d, 1H, 2.2 Hz); 8.03 (t, 1H, 2.2 Hz, 2.0 Hz); 7.43-7.59(m, 5H). 13CNMR(CDCl3, 75 MHz): δ 149.3,146.3, 138.2, 136.8, 136.2, 129.1, 128.6, 127.1, 120.8,

67.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; for 12h;Reflux;	In a 2000 mL round bottom flask, 3,5-dibromopyridine (30 g, 127 mmol), phenylboronic acid (18.53 g, 152 mmol), potassium carbonate (35.01 g, 253 mmol), tetrakistriphenylphosphine palladium (2.93 g, 1 mmol) 200 mL of water, 300 mL of toluene, and 300 mL of tetrahydrofuran were added and refluxed for 12 hours.When the reaction was completed, the mixture was cooled to room temperature, and then crystals were precipitated using methanol and filtered to obtain 20 g of the target product (yield 67.5%).
	With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In ethanol; water; toluene;	EXAMPLE 8 Sample No. 8 is (E)-N-Methyl-4-[3-(5-phenylpyridin)yl]-3-buten-1-amine, which is prepared according to the following procedure. 3-Bromo-5-phenylpyridine: A mixture of 3,5-dibromopyridine (15.00 g, 63.3 mmol), phenylboronic acid (8.11 g, 66.5 mmol), sodium carbonate (14.09 g, 133.0 mmol), water (100 mL), toluene (400 mL), absolute ethanol (100 mL), and tetrakis(triphenylphosphine)palladium(0) (3.66 g, 3.17 mmol) was stirred and heated under reflux at 92 C. (oil bath temperature) for 19 h. The mixture was cooled to ambient temperature and extracted with dichloromethane (400 mL). The dichloromethane layer was washed with saturated, aqueous NaHCO3 solution, dried (Na2 SO4), filtered, and concentrated to a residue. Vacuum distillation using a short-path apparatus produced 10.58 g of a white solid, bp 70-110 C. at 0.05 mm Hg (lit. bp 100-101 C. at ~0.1 mm Hg, see Guthikonda, R. N.; DiNinno, F. P. 2-(3-Pyridyl)carbapenam Antibacterial Agents. U.S. Pat. No. 5,409,920 (Merck and Co., Inc.), 950425).
	With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In ethanol; water; toluene;	EXAMPLE 3 Sample No. 3 is (E)-N-Methyl-4-[3-(5-phenylpyridin)yl]-3-buten- 1-amine, which is prepared according to the following procedure. 3-Bromo-5-phenylpyridine: A mixture of 3,5-dibromopyridine (15.00 g, 63.3 mmol), phenylboronic acid (8.11 g, 66.5 mmol), sodium carbonate (14.09 g, 133.0 mmol), water (100 mL), toluene (400 mL), absolute ethanol (100 mL), and tetrakis(triphenylphosphine)palladium(0) (3.66 g, 3.17 mmol) was stirred and heated under reflux at 92 C. (oil bath temperature) for 19 h. The mixture was cooled to ambient temperature and extracted with dichloromethane (400 mL). The dichloromethane layer was washed with saturated, aqueous NaHCO3 solution, dried (Na2 SO4), filtered, and concentrated to a residue. Vacuum distillation using a short-path apparatus produced 10.58 g of a white solid, bp 70-110 C. at 0.05 mm Hg (lit. bp 100-101 C. at ~0.1 mm Hg, see U.S. Pat. No. 5,409,920 to Guthikonda.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux;	[0541] Experimental Details: A mixture of 1 (5.2 g, 22 mmol) and 2 (2.44 g, 20 mmol) in an aqueous of 2 M Na2CO3 (25 mL) and toluene (40 mL) was stirred with Pd(PPh3)4 (0.57 g, 0.05 mmol) under reflux over night. The reaction mixture was extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was purified by column to give 3.
		Intermediate G6:; 5-Phenylpyridine-3-boronic acid; Step 1: 3-Bromo-5-phenyl-pyridine; Phenylboronic acid ( 0.618 g, 5.065 mmol) is stirred in a mixture of DME (20 ml) and 2M Na2COs for 20 minutes. 3,5-dibromopyridine (1.0 g, 4.221 mmol) is added followed by PdCl2(Ph3P)2 (0.296 g, 0.4221 mmol) and the mixture is heated to 100 C overnight. The DME layer is removed and is diluted with EtOAc, washing with 5M HCl (2 x 20 ml) then back extracted with EtOAc (70 ml). The acidic aqueous phase is basified with 6M NaOH (50 ml) and extracted with DCM ( 3 x 100 ml). The combined organic extracts are dried over MgSθ4, filtered and evaporated to an oil which is stirred in iso-hexanes (15 ml) and the resulting solid is removed washing with a further 10 ml of iso-hexanes. Concentration of the organics in vacuo affords the title compound as a white solid MH+ [235.74].
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Reflux;	Example 27 Experimental Details: A mixture of 1 (5.2 g, 22 mmol) and 2 (2.44 g, 20 mmol) in an aqueous of 2 M Na2CO3 (25 mL) and toluene (40 mL) was stirred with Pd(PPh3)4 (0.57 g, 0.05 mmol) under reflux over night. The reaction mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was purified by column to give 3.

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 10129 - 10137
[2]Patent: US2004/72823,2004,A1 .Location in patent: Page/Page column 20
[3]Patent: US2004/72823,2004,A1 .Location in patent: Page/Page column 15
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4145 - 4149
[5]Patent: KR102191780,2020,B1 .Location in patent: Paragraph 0407-0413
[6]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5820 - 5825
[7]Journal of Medicinal Chemistry,2000,vol. 43,p. 2217 - 2226
[8]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2825 - 2828
[9]Patent: US5861423,1999,A
[10]Patent: US5811442,1998,A
[11]Patent: WO2008/91681,2008,A2 .Location in patent: Page/Page column 240-241
[12]Patent: WO2009/10530,2009,A1 .Location in patent: Page/Page column 87
[13]Patent: US2010/16298,2010,A1 .Location in patent: Page/Page column 203

3
[ 625-92-3 ]
[ 591-50-4 ]
[ 142137-17-5 ]

Reference： [1]Synlett,2002,p. 1008 - 1010

4
[ 142137-17-5 ]
[ 349532-13-4 ]
[ 614751-57-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2825 - 2828

5
[ 142137-17-5 ]
2-(5-phenyl-pyridin-3-yl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2825 - 2828

6
[ 142137-17-5 ]
2-(5-phenyl-pyridin-3-yl)-9-aza-bicyclo[4.2.1]non-2-ene; hydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2825 - 2828

7
[ 625-92-3 ]
[ 110-71-4 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In dichloromethane; water;	3-Bromo-5-phenylpyridine: A mixture of 3,5-dibromopyridine (10.0 g, 42.2 mmol), phenylboronic acid (4.6 g, 38.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.25 mmol), potassium carbonate (17.5 g, 127 mmol), water (63 ml) and 1,2-dimethoxyethane (126 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (1 M, 60 ml) was added followed by extraction twice with diethyl ether (100 ml). Chromatography on silica gel with dichloromethane as solvent gave the title compound. Yield 6.1 g, 68%, Mp 42-44 C.
	With sodium hydroxide; potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In dichloromethane; water;	3-Bromo-5-phenylpyridine; (General Procedure for 3-Bromo-5-arylpyridines) A mixture of 3,5-dibromopyridine (10.0 g, 42.2 mmol), phenylboronic acid (4.6 g, 38.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.25 mmol), potassium carbonate (17.5 g, 127 mmol), water (63 ml) and 1,2-dimethoxyethane (126 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (1 M, 60 ml) was added followed by extraction twice with diethylether (100 ml). Chromatography on silica gel with dichloromethane as solvent gave the title compound. Yield 6.1 g, 68%, Mp 42-44 C.

Reference： [1]Patent: US2003/4153,2003,A1
[2]Patent: US6392045,2002,B1

Yield	Reaction Conditions	Operation in experiment
8.23 g (55.5%)		Further purification by column chromatography on silica gel, eluding with hexane-ethyl acetate (5:1, v/v) afforded 8.23 g (55.5%) of 3-bromo-5-phenylpyridine as a white solid, mp 45-46 C., Rf 0.50 (hexane-ethyl acetate (5:1, v/v)). 1 H NMR (CDCl3, 300 MHz): δ 8.74 (1H, d, J 1.7 Hz), 8.64 (1H, d, J=1.9 Hz), 8.01 (1H, t, J=2.0 Hz), 7.56-7.38 (5H, m). 13 C NMR (CDCl3, 75 MHz): δ 149.35, 146.38, 138.27, 136.86, 136.31, 129.20, 128.69, 127.18, 120.91. HRMS: Calcd. for C11 H8 BrN (M+*): m/z 232.984010. Found: 232.984177.
8.23 g (55.5%)		Further purification by column chromatography on silica gel, eluding with hexane-ethyl acetate (5:1, v/v) afforded 8.23 g (55.5%) of 3-bromo-5-phenylpyridine as a white solid, mp 45-46 C., Rf 0.50 (hexane-ethyl acetate (5:1, v/v)). 1 H NMR (CDCl3, 300 MHz): δ 8.74 (1H, d, J=1.7 Hz), 8.64 (1H, d, J=1.9 Hz), 8.01 (1H, t, J=2.0 Hz), 7.56-7.38 (5H, m). 13 C NMR (CDCl3, 75 MHz): δ 149.35, 146.38, 138.27, 136.86, 136.31, 129.20, 128.69, 127.18, 120.91. HRMS: Calcd. for C11 H8 BrN (M+): m/z 232.984010. Found: 232.984177.
66%Chromat.	With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100℃; for 12h;Inert atmosphere; Schlenk technique;Kinetics;	General procedure: 1,3-Dibromobenzene (Compound 1) 236 mg (1 mmol), phenylboronic acid 122 mg (1 mmol), toluene 5 mL, palladium acetate 4.5 mg (Pd atom 0.02 mmol, 0.02 relative to the amount of Compound 1 used Double molar Pd atom present), 4,5'-bis (diphenylphosphino) -9,9'-dimethylxanthene (Xantphos) 23 mg (0.04 mmol), and 2 prescribed tripotassium phosphate aqueous solution 925 mg (phosphorus) (2 mmol of tripotassium acid) was added to a 20 mL Schlenk tube, and the mixture was heated at 100 C. for 12 hours under a nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature, and the reaction solution was analyzed by GC (gas chromatograph) (internal standard = dibenzyl). The GC yield of the produced 3-bromobiphenyl (product 1) was 81%.

9
[ 627-27-0 ]
[ 6163-58-2 ]
[ 142137-17-5 ]
[ 212332-43-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;palladium diacetate; In acetonitrile;	(E)-4-[3-(5-Phenylpyridin)yl]-3-buten-1-ol: Under a nitrogen atmosphere, a mixture of 3-buten-1-ol (476 mg, 6.6 mmol), <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong> (1.50 g, 6.4 mmol), palladium(II) acetate (14.4 mg, 0.064 mmol), tri-o-tolylphosphine (78.0 mg, 0.256 mmol), triethylamine (2.5 mL), and acetonitrile (5.0 mL) was stirred and heated under reflux at 90 C. (oil bath temperature) for 18 h. Upon cooling to ambient temperature, the mixture was diluted with water (25 mL) and extracted with dichloromethane (4*25 mL). The combined dichloromethane extracts were washed with water (25 mL), dried (NaSO4), filtered, and concentrated by rotary evaporation to give a dark-green oil (1.69 g). Vacuum distillation using a test-tube apparatus gave 873 mg of a yellow oil, bp 60-80 C. at 0.05 mm Hg.
	With triethylamine;palladium diacetate; In acetonitrile;	(E)-4-[3-(5-Phenylpyridin)yl]-3-buten- 1-ol: Under a nitrogen atmosphere, a mixture of 3-buten-1-ol (476 mg, 6.6 mmol), <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong> (1.50 g, 6.4 mmol), palladium(II) acetate (14.4 mg, 0.064 mmol), tri-o-tolylphosphine (78.0 mg, 0.256 mmol), triethylamine (2.5 mL), and acetonitrile (5.0 mL) was stirred and heated under reflux at 90 C. (oil bath temperature) for 18 h. Upon cooling to ambient temperature, the mixture was diluted with water (25 mL) and extracted with dichloromethane (4*25 mL). The combined dichloromethane extracts were washed with water (25 mL), dried (Na2 SO4), filtered, and concentrated by rotary evaporation to give a dark-green oil (1.69 g). Vacuum distillation using a test-tube apparatus gave 873 mg of a yellow oil, bp 60-80 C. at 0.05 mm Hg.

Reference： [1]Patent: US5861423,1999,A
[2]Patent: US5811442,1998,A

10
[ 625-92-3 ]
[ 497-19-8 ]
[ 98-80-6 ]
[ 142137-17-5 ]

Yield	Reaction Conditions	Operation in experiment
28%	tetrakis(triphenylphosphine) palladium(0); In ethanol; hexane; ethyl acetate; toluene;	Preparation of Intermediate Synthons 3-Bromo-5-phenylpyridine STR34 Tetrakis(triphenylphosphine)palladium (577 mg; 0.5 mM) was added to 3,5-dibromopyridine (5.214 g; 22 mM) in 40 mL of toluene at R.T. under nitrogen. After 10 minutes stirring, 25 mL of 2M aqueous sodium carbonate solution, phenylboronic acid (2.44 g; 20 mM), and 10 mL of ethanol were added, and the mixture was heated 11 hours at 80 C. The reaction mixture was cooled, diluted with 75 mL of ethyl acetate and washed with 2*15 mL of saturated sodium carbonate solution, and then dried over anhydrous magnesium sulfate. Solvent removal gave crude product, which was chromatographed on silica gel using ethyl acetate:hexane (1:5) mixture to give a white solid boiling at 100-101 C./~0.1 mm in 28% yield.

Reference： [1]Patent: US5409920,1995,A

11
[ 625-92-3 ]
palladium tetra(triphenylphosphine) [ No CAS ]
[ 98-80-6 ]
[ 142137-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	25a. 3-bromo-5-phenylpyridine Portions of 3,5-dibromopyridine (1.0 g, 4.22 mmol), phenylboronic acid (570 mg, 4.6 mmol) and palladium tetra(triphenylphosphine) (60 mg) were combined in toluene (20 mL) with aqueous sodium carbonate solution (2M, 3.0 mL) and heated at reflux for 6 hours. The mixture was cooled to ambient temperature, and the solvent was removed. The residue was purified by chromatography (silica gel, eluding with ether:hexane 1:10 to give the title compound: MS (CI/NH3) m/z: 234/236 (M+H)+, 251/153 (M+NH4)+; 1 H NMR (CDCl3, 300 MHz) δ7.21-8.02 (dd, J=2.0, 2.0 Hz), 8.65 (d, J=2.0 Hz), 8.75 (d, J=2.0 Hz).

Reference： [1]Patent: US5733912,1998,A

12
[ 142137-17-5 ]
[ 850991-38-7 ]

Yield	Reaction Conditions	Operation in experiment
		[0543] Experimental Details: A solution of compound 3 (0.78 g, 3.3 mmol) and triisopropyl borate (1 mL, 4 mmol) in anhydrous toluene ( 50 mL) was treated with n-BuLi ( 1.5 mL, 3.75 mmol) at -60 C under N2 atmosphere. After complete addition, theis mixture was stirred at -10 C for 1 h. The reaction mixture was quenched by adding aqueous of 2 M HCl, and washed with toluene. The aqueous layer was brought pH = 8 by adding Na2CO3, extracted then with ethyl acetate (50 mL * 3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was separated by column to give 4.

Reference： [1]Patent: WO2008/91681,2008,A2 .Location in patent: Page/Page column 241
[2]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673

13
[ 156641-98-4 ]
[ 142137-17-5 ]
[ 1050646-68-8 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5064 - 5074

14
[ 5419-55-6 ]
[ 142137-17-5 ]
[ 850991-38-7 ]

Yield	Reaction Conditions	Operation in experiment
		Experimental Details: A solution of compound 3 (0.78 g, 3.3 mmol) and triisopropyl borate (1 mL, 4 mmol) in anhydrous toluene ( 50 mL) was treated with n-BuLi (1.5 mL, 3.75 mmol) at -60 C. under N2 atmosphere. After complete addition, theis mixture was stirred at -10 C. for 1 h. The reaction mixture was quenched by adding aqueous of 2 M HCl, and washed with toluene. The aqueous layer was brought pH=8 by adding Na2CO3, extracted then with ethyl acetate (50 mL×3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was separated by column to give 4.

Reference： [1]Patent: US2010/16298,2010,A1 .Location in patent: Page/Page column 203-204

15
[ 1194459-23-8 ]
[ 142137-17-5 ]
[ 1194450-14-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2307 - 2319

16
[ 1279123-63-5 ]
[ 13675-18-8 ]
[ 142137-17-5 ]
[ 1386231-79-3 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673

17
[ 108-86-1 ]
[ 142137-17-5 ]
[ 92-07-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673

18
[ 142137-17-5 ]
[ 1386231-79-3 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673

19
[ 909135-34-8 ]
[ 142137-17-5 ]
C₂₄H₂₈N₂O₂*ClH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9929 - 9945

20
[ 909135-34-8 ]
[ 142137-17-5 ]
C₁₉H₂₀N₂*ClH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9929 - 9945

21
[ 13535-01-8 ]
[ 591-50-4 ]
[ 73183-34-3 ]
[ 142137-17-5 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 1923 - 1933

22
[ 85908-96-9 ]
[ 142137-17-5 ]
[ 1446750-53-3 ]

Yield	Reaction Conditions	Operation in experiment
61%		Asolution of <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong> (10)(975 mg, 4.16 mmol) in diethyl ether (10 mL) was added dropwise over 10 min toa solution of nBuLi (1.4 M inhexanes, 2.97 mL, 4.16 mmol) in diethyl ether (15 mL) at -78 C and the mixturewas stirred at -78 C for 20 min. Asolution of Boc-protected δ-valerolactam 11) (829 mg, 4.16 mmol) in diethylether (8 mL) was added and the mixture was further stirred at -78 C for 2 hand at 0 C for 5 min. The reaction wasquenched with 2M HCl to pH 1-2, and the mixture was extracted with diethylether. The combined organic layers werewashed twice with 10 % aqueous solution of sodium bicarbonate, dried over Na2SO4, filtered, and the solvents were evaporated. The crude was purified by chromatographycolumn, using a gradient of hexanes/ethyl acetate 10:1 to 3:1as eluent to yieldthe product as yellowish solid (900 mg, 61 %). 1HNMR (CDCl3, 300 MHz): δ 9.13(d, 1H, 2.2 Hz); 9.01 (d, 1H, 2.2 Hz); 8.42 (t, 1H, 2.2 Hz); 7.60-7.64 (m, 2H);7.42-7.54 (m, 3H); 4.68 (br s, 1H); 3.16-3.22 (m, 2H); 3.09 (t, 2H, 7.0 Hz);1.78-1.88 (m, 2H); 1.56-1.66 (m, 2H); 1.44 (s, 9H) 13CNMR(CDCl3, 75 MHz): δ 198.6,155.9, 151.6, 147.8, 136.7, 136.5, 133.4, 131.9, 129.1, 128.5, 127.1, 79.0,40.1, 38.4, 29.5, 28.3, 20.8. IR (neat): 3369 cm-1,1685 cm-1, 1516 cm-1, 1248 cm-1, 1162 cm-1. HRMS (ESI): [M+H]+calculated:355.2016, found: 355.2007; [M+Na]+ calculated: 377.1836,found: 377.1835

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4145 - 4149

23
[ 937591-32-7 ]
[ 142137-17-5 ]
[ 1593884-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5179 - 5189

24
[ 142137-17-5 ]
[ 1008-88-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 25℃; for 1.5h;Inert atmosphere;	General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 393,p. 191 - 209

25
[ 625-92-3 ]
[ 603-33-8 ]
[ 142137-17-5 ]

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

26
[ 123-07-9 ]
[ 142137-17-5 ]
3-(4-ethylphenoxy)-5-phenylpyridine [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 426 - 429

27
[ 142137-17-5 ]
8-ethyl-3-phenylbenzofuro[3,2-b]pyridine 1-oxide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 426 - 429

28
[ 142137-17-5 ]
8-ethyl-3-phenylbenzofuro[3,2-b]pyridine [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 426 - 429

29
[ 142137-17-5 ]
3-(4-ethylphenoxy)-5-phenylpyridine 1-oxide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 426 - 429

30
[ 1464115-37-4 ]
[ 142137-17-5 ]
[ 1404367-02-7 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2530 - 2537

31
4,4'-sulfonylbis(4,1-phenylene)bis(trimethylstannane) [ No CAS ]
[ 142137-17-5 ]
5,5'-(4,4'-sulfonylbis(4,1-phenylene))bis(3-phenylpyridine) [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 10129 - 10137

32
[ 771-99-3 ]
[ 142137-17-5 ]
C₂₂H₂₂N₂ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3370 - 3373

33
[ 7732-18-5 ]
[ 142137-17-5 ]
[ 31676-55-8 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3370 - 3373

34
[ 766-77-8 ]
[ 142137-17-5 ]
1-(dimethyl(phenyl)silyl)-3-methyl-5-phenyl-1,4-dihydropyridine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15176 - 15184

35
[ 142137-17-5 ]
(E)-3-bromo-5-phenyl-2-styrylpyridine [ No CAS ]
C₁₉H₁₄BrN [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5820 - 5825

36
[ 142137-17-5 ]
3-bromo-5-phenylpyridine N-oxide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5820 - 5825

37
[ 142137-17-5 ]
(E)-3-(5-phenylpyridin-3-yl)acrylic acid [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 984 - 987

38
[ 142137-17-5 ]
C₁₄H₁₁NO₃ [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 984 - 987

39
[ 142137-17-5 ]
6-phenyl-2H-pyrano[2,3-b]pyridin-2-one [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 984 - 987

40
[ 292638-85-8 ]
[ 142137-17-5 ]
methyl (E)-3-(5-phenylpyridin-3-yl)acrylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 984 - 987

41
[ 142137-17-5 ]
3-(2-oxo-2-phenylethyl)-5-phenylpyridine 1-oxide [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 4100 - 4110

42
[ 142137-17-5 ]
1-benzyl-2,5-diphenyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 4100 - 4110

43
[ 98-86-2 ]
[ 142137-17-5 ]
1-phenyl-2-(5-phenylpyridin-3-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; for 15h;Sealed tube; Inert atmosphere; Reflux;	In a sealed tube equipped with magnetic stir bar was combined Pd(OAc)2 (67 mg, 0.3 mmol), P(tBu)3·HBF4 (35 mg, 0.12 mmol), t-BuONa (1.44 g, 14.95 mmol) and degassed anhydrous THF (31 ml). After stirring for 5 min under argon, <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong> (1.40 g, 5.98 mmol) and acetophenone (1.08 g, 8.97 mmol) were added. The resulting mixture was heated to reflux for 15 h. After cooled down to r. t, the mixture was diluted with DCM and water, filtered through Celite, and the filtrate was separated. Water phase was extracted with DCM. The combined organic phase was dried, concentrated in vacuo to give the crude product, which was chromatographed gradiently on silica gel with PE/EA (30:1-10:1) to afford 10i (750 mg, 46 % yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.76 (d, J=2.0Hz, 1H), 8.51 (d, J=2.0Hz, 1H), 8.05 (d, J=7.2Hz, 2H), 7.80 (s, 1H), 7.63-7.57 (m, 3H), 7.52-7.45 (m, 4H), 7.40 (d, J=7.2Hz, 1H), 4.37 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 196.5, 149.4, 147.1, 137.8, 136.6, 136.4, 135.8, 133.7, 130.2, 129.2, 129.0, 128.6, 128.3, 127.4, 42.4. HRMS (+ESI-TOF) m/z: [M + H] + calcd for C19H16NO 274.1226; found 274.1217.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4100 - 4110

44
[ 110-89-4 ]
[ 142137-17-5 ]
[ 1008-88-4 ]
3-phenyl-5-(piperidin-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%; 23%	With sodium hydride; lithium iodide; In tetrahydrofuran; mineral oil; at 60℃; for 3h;Inert atmosphere; Sealed tube;Mechanism;	General procedure: To a mixture of NaH (60% dispersion, 100 mg, 2.50 mmol) and LiI (134 mg, 1.00 mmol) in a 25-mL sealed tube was added a solution of arene substrate (0.50 mmol) in THF (0.5 mL) and piperidine (85.2 mg, 99 μL,1.00 mmol). The reaction was stirred at 60 C (the reaction time is indicated in the respective scheme) and was quenched with water at 0 C. The organic materials were extracted with CH2Cl2 (3 × 20 mL).The combined organic extracts were washed brine and dried ,(MgSO4). The volatile materials were removed in vacuo and the resulting crude residue was purified by flash column chromatography (the eluent system is indicated for each substrate) to give the product.

Reference： [1]Synthesis,2020,vol. 52,p. 393 - 398

45
[ 142137-17-5 ]
2-phenyl-3-{4-[10-(5-phenyl-3-pyridyl)-9-anthryl]phenyl}quinoxaline [ No CAS ]

Reference： [1]Patent: WO2020/194097,2020,A1
[2]Patent: JP2020/158497,2020,A

46
[ 142137-17-5 ]
3-(10-bromo-9-anthryl)-5-phenylpyridine [ No CAS ]

Reference： [1]Patent: WO2020/194097,2020,A1
[2]Patent: JP2020/158497,2020,A

47
[ 100622-34-2 ]
[ 142137-17-5 ]
3-(9-anthryl)-5-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 80℃; for 14h;Inert atmosphere;	Into a 200 mL three-neck flask were added 1.0 g (4.3 mmol) of <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong>, 2.0 g (9.2 mmol) of 9-anthraceneboronic acid, and 2.4 g (17 mmol) of potassium carbonate, and the air in the flask was replaced with nitrogen. Into the mixture were added 40 mL of tetrahydrofuran and 8 mL of water, and the mixture was degassed by being stirred under reduced pressure. Into the mixture were added 0.10 g (0.35 mmol) of tri-tert- butylphosphoniumtetrafluoroborate and 98 mg (0.11 mmol) of tris(dibenzylideneacetone)dipalladium(0), and the mixture was stirred under a nitrogen stream at 80 C for 14 hours. After the stirring, water was added to the mixture, followed by extraction of an aqueous layer with toluene. The obtained solution of the extract and an organic layer were combined and washed with water and brine, and an organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (toluene: ethyl acetate = 9:1) and recrystallized with methanol to give 1.4 g of a target white solid in a yield of 98 %. Synthesis Scheme (e-1) is shown below.
98%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 80℃; for 14h;Inert atmosphere;	Add 1.0 g (4.3 mmol) of <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong>, 2.0 g (9.2 mmol) of 9-anthracene boronic acid, and 2.4 g (17 mmol) of potassium carbonate to a 200 mL three-necked flask and replace the inside of the flask with nitrogen. did. 40 mL of tetrahydrofuran and 8 mL of water were added to this mixture, and the mixture was degassed by stirring under reduced pressure. To this mixture was added 0.10 g (0.35 mmol) of tri-tert-butylphosphonium tetrafluoroborate and 98 mg (0.11 mmol) of tris (dibenzylideneacetone) dipalladium (0), and under a nitrogen stream at 80 C. for 14 hours. Stirred.After stirring, water was added to the mixture and the aqueous layer was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was naturally filtered and the filtrate was concentrated to give a solid. This solid was purified by silica gel column chromatography (toluene: ethyl acetate = 9: 1) and recrystallized from methanol to obtain 1.4 g of the desired white solid in a yield of 98%.

Reference： [1]Patent: WO2020/194097,2020,A1 .Location in patent: Paragraph 0324; 0326-0328
[2]Patent: JP2020/158497,2020,A .Location in patent: Paragraph 0324-0328

48
C₁₁H₅BrClNO [ No CAS ]
[ 142137-17-5 ]
C₂₂H₁₃ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; for 12h;Reflux;	In a 500 mL round bottom flask (10 g, 35 mmol), (9.95 g, 35 mmol), potassium carbonate (9.078 g, 71 mmol), tetrakistriphenylphosphine palladium (0.82 g, 1 mmol) 50 mL of water, 100 mL of toluene and 100 mL of tetrahydrofuran were added and refluxed for 12 hours.When the reaction was completed, the mixture was cooled to room temperature, and then crystals were precipitated using methanol and filtered to obtain 6.3 g (yield 50%) of the target product.

Reference： [1]Patent: KR102191780,2020,B1 .Location in patent: Paragraph 0407; 0420-0425

49
C₁₁H₅BrClNO [ No CAS ]
[ 142137-17-5 ]
C₅₁H₃₁N₅O [ No CAS ]

Reference： [1]Patent: KR102191780,2020,B1

50
N-((2R,3S)-2-(((cis-4-phenylcyclohexyl)oxy)methyl)piperidin-3-yl)methanesulfonamide [ No CAS ]
[ 142137-17-5 ]
N-((cis)-2-((((cis)-4-phenylcyclohexyl)oxy)methyl)-1-(5-phenylpyridin-3-yl)piperidin-3-yl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) oxide; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 2-fluoro-6-(piperidine-1-sulfonyl)anilino(oxo)acetic acid; In dimethyl sulfoxide; at 100℃; for 24h;Sealed tube;	To a one mL vial (placed in a 24 well gold aluminum block) containing a stir bar was added 3-bromo-5-phenyl pyridine (3.51 mg, 0.015 mmol), 2-fluoro-6-(piperidine-1- sulfonyl)anilino(oxo)acetic acid (2.64 mg, 0.008 mmol), copper (I) oxide (16 ml of 0.5 M DMSO solution, 1.13 mg, 0.008 mmol), I-((CIS)-2-((((CIS)-4-phenylcyclohexyl)oxy)methyl)piperidin-3- yl)methanesulfonamide (4.80 mg, 0.01 mmol), 2-tert-butyl-1,l,3,3-tetramethyl guanidine (6 ml, 0.03 mmol). The plate was sealed and the reaction mixture was stirred at 100 C for 24 h. The reaction mixture was allowed to cool to room temperature, diluted with about 1084 mL of DMSO and filtered. The filtrate was chromatographed using preparative HPLC reverse phase C18 (Acetonitrile/Water + 0.1% TFA) to afford the title compound. MS: 520.18 (M+l).

Reference： [1]Patent: WO2021/26047,2021,A1 .Location in patent: Page/Page column 99-100

51
N-((cis)-2-((((cis)-4-phenylcyclohexyl)oxy)methyl)pyrrolidin-3-yl)methanesulfonamide [ No CAS ]
[ 142137-17-5 ]
N-((cis)-2-((((cis)-4-phenylcyclohexyl)oxy)methyl)-1-(5-phenylpyridin-3-yl)pyrrolidin-3-yl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) oxide; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 2-fluoro-6-(piperidine-1-sulfonyl)anilino(oxo)acetic acid; In dimethyl sulfoxide; at 100℃; for 14h;	To a one mL vial (placed in a 24 well gold aluminum block) containing a stir bar was added 3-bromo-5-phenyl pyridine (20 ml of 0.5M DMSO solution, 2.34 mg, 0.01 mmol), 2- fluoro-6-(piperidine-1-sulfonyl)anilino(oxo)acetic acid (8 ml of 1.0 M DMSO solution, 2.64 mg, 0.008 mmol), copper (I) oxide (16 ml of 0.5 M DMSO solution, 1.13 mg, 0.008 mmol), I-((CIS)-2-((((CIS)-4-phenylcyclohexyl)oxy)methyl)pyrrolidin-3-yl)methanesulfonamide (20 ml of 0.5 M DMSO solution, 4.66 mg, 0.01 mmol), DMSO (30 ml), 2-tert-butyl-1,l,3,3-tetramethyl guanidine (6 ml, 0.03 mmol). The plate was sealed and the reaction mixture was stirred at 100 C for 14 h. The reaction mixture was allowed to cool to room temperature, diluted with about 1 mL of DMSO and filtered. The filtrate was chromatographed using preparative HPLC reverse phase C18 (Acetonitrile/ Water + 0.16% TFA) to afford the title compound. MS: 506.24 (M+l). 1H NMR (500 MHz, DMSO-d6) d 8.44 (d, J = 1.26, 1H), 8.29 (d, J = 2.60, 1H), 7.97 (s, 1H), 7.84 (dd, J = 7.75, 1.30, 2H), 7.59 - 7.52 (m, 4H), 7.20-7.12 (m, 3H), 6.89 (d, J = 7.00 Hz, 2H), 4.54 - 4.51 (td, J = 7.50, 3.23, 1H), 4.13 - 4.08 (m, 1H), 3.87 - 3.43 (m, 5H), 3.09 (s, 3H), 2.46 - 2.35 (m, 2H), 2.28 - 2.19 (m, 1H), 1.92-1.79 (m, 2H), 1.56 - 1.28 (m, 6H).

Reference： [1]Patent: WO2021/26047,2021,A1 .Location in patent: Page/Page column 78-79

52
[ 1008-88-4 ]
[ 142137-17-5 ]

Reference： [1]Patent: CN113527188,2021,A

53
3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dihydropyridine [ No CAS ]
[ 142137-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-bromosaccharin; In tetrahydrofuran; at 40℃; for 12h;	S2, the system is cooled to room temperature, and 104.0 mg (0.4 mmol, 2.0 equiv) of N-bromosaccharin (2f) is added to the reaction vial and reacted at 40 C for 12 hours. The reaction formula is as follows:

Reference： [1]Patent: CN113527188,2021,A .Location in patent: Paragraph 0035-0038

54
[ 142137-17-5 ]
Methyl 4-fluoro-3-((5-phenylpiperidin-3-yl)oxy)benzoate [ No CAS ]

Reference： [1]Patent: WO2021/216592,2021,A1

55
[ 142137-17-5 ]
cis-methyl 4-fluoro-3-((1-(methylsulfonyl)-5-phenylpiperidin-3-yl)oxy)benzoate [ No CAS ]

Reference： [1]Patent: WO2021/216592,2021,A1

56
[ 142137-17-5 ]
[ 214822-96-5 ]
Methyl 4-fluoro-3-((5-phenylpyridin-3-yl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.9%	With copper(l) iodide; dimethylaminoacetic acid; caesium carbonate; In 1,4-dioxane; at 100℃; for 24h;Inert atmosphere;	To a stirred solution of <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong> (2.0 g, 8.54 mmol, 1.00 equiv) in dioxane (40 mL) under nitrogen were added methyl 4-fluoro-3-hydroxybenzoate (2.91 g, 17.1 mmol, 2.00 equiv) and dimethylglycine (441 mg, 4.27 mmol, 0.50 equiv). To the above solution were added CS2CO3 (8.35 g, 25.6 mmol, 3.00 equiv) and Cul (814 mg, 4.27 mmol, 0.50 equiv). The reaction mixture was stirred for 24 h at 100C. The reaction was quenched with H2O (200 mL). The mixture was extracted with EtOAc (3x200 mL) and the combined organic layers dried over anhydrous Na2SO4and concentrated under vacuum. The residue was eluted from silica gel with EtO Ac/PE (1:10). This resulted in 800 mg (28.9%) of the title compound as yellow oil. MS-ESI: 324 (M+l).

Reference： [1]Patent: WO2021/216592,2021,A1 .Location in patent: Paragraph 220-222

57
[ 1218791-02-6 ]
[ 142137-17-5 ]
C₁₉H₁₄N₄ [ No CAS ]

Reference： [1]ChemPlusChem,2022,vol. 87

58
[ 142137-17-5 ]
[ 98-80-6 ]
[ 92-07-9 ]

Reference： [1]ChemPlusChem,2022,vol. 87

59
[ 5720-07-0 ]
[ 142137-17-5 ]
3-phenyl-5-(p-anisyl)-pyridine [ No CAS ]

Reference： [1]ChemPlusChem,2022,vol. 87

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Similarity: 0.98

[ 142337-95-9 ]

3-Bromo-5-ethylpyridine

Similarity: 0.96

[ 27063-98-5 ]

3-Bromo-4,5-dimethylpyridine

Similarity: 0.91

[ 38749-76-7 ]

3-Bromo-4-ethylpyridine

Similarity: 0.91

[ 1209459-74-4 ]

3-Bromo-5-isopropylpyridine

Similarity: 0.90

Related Parent Nucleus of
[ 142137-17-5 ]

Pyridines

[ 118775-69-2 ]

3-Bromo-5-(prop-1-en-2-yl)pyridine

Similarity: 0.98

[ 142337-95-9 ]

3-Bromo-5-ethylpyridine

Similarity: 0.96

[ 27063-98-5 ]

3-Bromo-4,5-dimethylpyridine

Similarity: 0.91

[ 38749-76-7 ]

3-Bromo-4-ethylpyridine

Similarity: 0.91

[ 1209459-74-4 ]

3-Bromo-5-isopropylpyridine

Similarity: 0.90

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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. 142137-17-5 ] {[proInfo.proName]}

Quality Control of [ 142137-17-5 ]

Related Doc. of [ 142137-17-5 ]

Product Details of [ 142137-17-5 ]

Calculated chemistry of [ 142137-17-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 142137-17-5 ]

Application In Synthesis of [ 142137-17-5 ]

[ 142137-17-5 ] Synthesis Path-Upstream 1~9

[ 142137-17-5 ] Synthesis Path-Downstream 1~59

Related Functional Groups of [ 142137-17-5 ]

Aryls

Bromides

Related Parent Nucleus of [ 142137-17-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 142137-17-5 ]

Related Parent Nucleus of
[ 142137-17-5 ]