42260-39-9|2-Chloro-4-phenylpyridine| Ambeed

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Quality Control of [ 42260-39-9 ] Purity: 97% SDS Specification

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Product Details of [ 42260-39-9 ]

CAS No. :	42260-39-9
Formula :	C₁₁H₈ClN
M.W :	189.64
SMILES Code :	ClC1=NC=CC(C2=CC=CC=C2)=C1
MDL No. :	MFCD04114163
InChI Key :	MROTUXXYBNRZSG-UHFFFAOYSA-N
Pubchem ID :	2762842

Safety of [ 42260-39-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 42260-39-9 ] Show Less

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	54.68
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.22
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.44
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.4
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.68
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.08

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.8
Solubility	0.0301 mg/ml ; 0.000158 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.39
Solubility	0.077 mg/ml ; 0.000406 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.16
Solubility	0.00131 mg/ml ; 0.00000692 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.01 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.59

Application In Synthesis of [ 42260-39-9 ]

* 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.

Downstream synthetic route of [ 42260-39-9 ]

[ 42260-39-9 ] Synthesis Path-Downstream 1~35

1
[ 42260-39-9 ]
[ 108-42-9 ]
(3-Chloro-phenyl)-(4-phenyl-pyridin-2-yl)-amine [ No CAS ]

References: [1]Archiv der Pharmazie,1996,vol. 329,p. 371 - 376.

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 80℃; for 24h;Inert atmosphere;	General procedure: 2-bromo-6-chloropyridine (21.2 g, 0.11 mol)Phenylboronic acid (12.2 g, 0.10 mol)Palladium tetrakis triphenylphosphine 0.5g,Add to 1000ML reaction flask, add toluene 400ML,Aqueous sodium carbonate solution (2N, 150 mL) was treated with nitrogen and the oil bath was reacted at 80 ° C for 24 hours.Post-treatment: cooling, static 30 minutes to remove the liquid, keep the organic layer, spin dry toluene, solid plus dichloromethane dissolved, column separation, PE: DCM = 1: 1 column, was A-1 (9.6g, Y = 51percent)

3
[ 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)+.

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

4
[ 153034-86-7 ]
[ 98-80-6 ]
[ 42260-39-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate;dichloro[di-tert-butyl(chloro)phosphine]palladium(II) dimer; In methanol; for 3.00833h;	Example 1; 4-Aminomethyl-cyclohexanecarboxylic acid [2-phenyl-1-(4-phenyl-pyridin-2-yl)- ethyl] -amide, bistrifluoroacetic acid salt; [00335] lA. 2-Chloro-4-phenylpyridine: A flask was charged with 2-chloro- 4-iodo pyridine (2.5g, 10.4 mmol), phenylboronic acid (1.33 g, 10.96 mmol) , K2C03 (4.54 g, 32.88 mmol), PXPd2 (0.186 g, 0.261 mmol), and methanol (34.8 mL). Argon was blown through flask for 30 sec. The dark brown suspension was stirred for 3 h and then filtered, washing with methanol. The filtrate was concentrated to give 2.15 g as a brown solid. Column chromatography (120g silica gel column; gradient elution; 0-35% ethyl acetate/hexane) afforded lA (1.79 g, 90%) as a yellow solid. iH-NMR (400 MHz, CDCI3) 8: 8.43 (d, J = 5.3 Hz, 1H), 7.61 (dd, J = 8.2, 1.5 Hz, 2H), 7.54 (d, J = 2.2 Hz, 1H), 7.52-7.47 (m, 3H), 7.43 (dd, J = 5.1, 1.5 Hz, 1H). ¹3C-NMR (125 MHz, CDC13) No.: 152.2, 151.5, 149.9, 136.8, 129.6,129.2, 127.0, 122.0,120.4. MS 190.0 (M+H) + and 192.0 (M+2+H)+.
84%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; for 2h;Inert atmosphere; Reflux;	To a mixture of 1 (57.36 g, 0.24 mol) in THF/H2O (400 mL/100 mL) were added phenylboric acid (24.2 g, 0.2 mol) and K2CO3 (82.8 g, 0.6 mol). PdCl2(dppf) (2 g) was then added after being charged with N2 three times. The resulting mixture was refluxed for 2 hrs, cooled, and partitioned between a.q. NH4C1 and EtOAc. The aqueous layer was washed with EtOAc. The combined organic layers were washed with water, brine and dried over Na2 S O4. The solvent was removed in vacuo and the residue was purified by silica gel column (PE:EA=10: 1) to afford 32 g of 2 (yield 84%).
82%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux;	A mixture of 2-chloro-4-iodopyridine (20.0 g, 82 mmol), phenylboronicacid (10.2 g, 82 mmol), Pd(Ph3P)4 (2.84 g 2.46 mmol), sodium carbonate (26.0 g, 246 mmol), DME (600 mL) andwater (150 mL) was degassed with nitrogen and then refluxed overnight. The reaction was concentrated and the extractedwith ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then vacuum distilled to give 2-chloro-4-phenylpyridine(2.79 g, 12.7 mmol, 82 % yield).

51%

With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux;

To a 1 L three-necked flask were added 2-chloro-4-iodopyridine (50 g, 208.8 mmol), phenyl boronic acid (28 g, 229.7 mmol), Pd(PPh3)4 (12 g, 10.4 mmol), potassium carbonate (86 g, 626 mmol), toluene (500 mL) and water (200 mL), and then the resulting reaction mixture was heated to reflux for 12 h under N2 protection. Then the reaction solution was cooled to room temperature, separated, the organic phase was collected, the water phase was extracted with EA for several times, and the organic phase was combined, dried with MgSO4 and evaporated to dryness, purified via silica gel column chromatography, eluting with EA:PE=1:50 (v:v), to afford intermediate 1 (20 g, 51% yield) as a white solid.

References: [1]Inorganic Chemistry,2017,vol. 56,p. 8244 - 8256.
[2]Patent: WO2005/123680,2005,A1 .Location in patent: Page/Page column 76.
[3]Patent: WO2010/94242,2010,A1 .Location in patent: Preparation III.1.
[4]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0229; 0230.
[5]Patent: US2019/225635,2019,A1 .Location in patent: Paragraph 0132; 0133.

5
[ 42260-39-9 ]
[ 82278-36-2 ]
2-{4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; at 300 - 350℃; for 0.05h;	Step c: Preparation of 2-{4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine In a test tube, 0.38 g (2.0 mmol) of <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong>, 0.6 g (2.0 mmol) of 4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]butylamine and a spatula tipful of 4-dimethylaminopyridine are heated to approximately 300-350° C. for 3 minutes. The mixture is diluted with ethyl acetate and chromatographed on silica gel (eluent: dichloromethane/ethanol 90/10). After concentration of the elution fractions, the product crystallises. After comminution in diethyl oxide, filtration and drying, 80 mg of 2-{4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine are obtained in the form of a white solid. Melting point: 120° C. (tube) 1H NMR (CDCl3): 8.1 (doublet, 1H); 7.65 to 7.55 (unresolved peaks, 2H); 7.5 to 7.25 (unresolved peaks, 4H); 7.2 to 7.0 (unresolved peaks, 3H); 6.8 (doublet, 1H); 6.55 (singlet, 1H); 4.8 (wide triplet, 1H); 3.35 (multiplet, 2H); 3.35 to 3.15 (unresolved peaks, 4H); 2.7 to 2.55 (unresolved peaks, 4H); 2.45 (triplet, 2H); 1.85 to 1.65 (unresolved peaks, 4H)

References: [1]Patent: US2006/89364,2006,A1 .Location in patent: Page/Page column 12.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5376 - 5379.

6
[ 42260-39-9 ]
[ 883874-73-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 5 - 20℃;	Step a: Preparation of <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong>-1-oxide 10.73 g (62.2 mmol) of meta-chloroperbenzoic acid are added in portions to a solution of 3.3 g (17.4 mmol) of <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> in 35 mL of dichloromethane cooled to 5° C. The suspension is stirred overnight at ambient temperature. The reaction medium is diluted with 150 mL of ethyl acetate and washed successively with water, with a saturated aqueous sodium metabisulfite solution, with a saturated aqueous sodium carbonate solution and with water. The organic phase is then dried over magnesium sulfate, filtered and concentrated. The solid residue is stirred with an acetonitrile/diisopropyl oxide mixture, filtered and dried under a vacuum. Yield: 51percent Melting point: 152° C. 1H NMR (CDCl3): 8.4 (doublet, 1H, J=6.7 Hz); 7.7 (d, 1H, J=2.5 Hz); 7.65 to 7.35 (unresolved peaks, 6H).

References: [1]Organic Letters,2015,vol. 17,p. 3726 - 3729.
[2]Patent: US2006/89364,2006,A1 .Location in patent: Page/Page column 18.

7
[ 42260-39-9 ]
[ 189061-44-7 ]
2-{4-[4-(2,3-fluorophenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4%	With dmap; for 0.0666667h;Microwave irradiation;	Step c: Preparation of 2-{4-[4-(2,3-fluorophenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine In a test tube, 0.19 g (2.0 mmol) of <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong>, 0.3 g (1.0 mmol) of 4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butylamine and a spatula tipful of 4-dimethylaminopyridine are heated for 4 minutes in a microwave oven. The mixture is diluted with ethyl acetate and chromatographed on silica gel (eluent: ethyl acetate/ethanol). After concentration of the elution fractions, 20 mg (4percent) of 2-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine are obtained in the form of a yellowish viscous oil. 1H NMR (CDCl3): 8.15 (doublet, 1H); 7.65 to 7.5 (unresolved peaks, 2H); 7.5 to 7.35 (unresolved peaks, 3H); 7.2 to 7.05 (unresolved peaks, 2H); 6.9 (multiplet, 1H); 6.75 (multiplet, 1H); 6.55 (singlet, 1H); 4.9 (wide singlet, 1H); 3.4 (triplet, 2H); 3.2 to 3.0 (unresolved peaks, 4H); 2.8 to 2.5 (unresolved peaks, 4H); 2.5 (triplet, 2H); 1.8 to 1.6 (unresolved peaks, 4H)

References: [1]Patent: US2006/89364,2006,A1 .Location in patent: Page/Page column 14.

8
[ 42260-39-9 ]
[ 1029719-05-8 ]
[ 1029719-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In 1,4-dioxane; at 100℃; for 3h;	N-[(S)-2-(4-Amino-phenyl)-1 -{(R)-3-[1 -(3-isopropyl-phenyl)-cyclopropyl]-2-oxo-oxazolidin-5- yl}-ethyl]-acetamide (100 mg, 0.237 mmol), <strong>[42260-39-9]2-chloro-4-phenyl-pyridine</strong> (63 mg, 0.33 mmol), Pd2(dba)3 (1 1 mg, 0.012 mmol), 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl (9.3 mg, 0.24 mmol) and sodium tert-butoxide (35 mg, 0.36 mmol) are dissolved in dry dioxane (2.0 ml). The reaction mixture is heated to 100 °C for 3 h, then cooled to RT and filtered over a bed of Celite. The filter cake is washed with EtOAc, and the combined filtrates are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified on silica to give the title compound [HPLC Rt8 = 4.08 min; ESIMS [M-H]+ = 575].

References: [1]Patent: WO2008/62044,2008,A1 .Location in patent: Page/Page column 24.

9
[ 67-56-1 ]
[ 42260-39-9 ]
[ 201230-82-2 ]
[ 18714-17-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 70℃; under 30003.0 Torr;	To a solution of 2 (2 g, 0.01 mol) in MeOH (100 mL) were added TEA (5.33 g, 0.05 mol) andPdCl2(dppf) (0.5 g). The reaction mixture was stirred overnight at 70 °C under 4 MPa CO. The suspension was filtered through a pad of celite and washed with MeOH. The combined filtrates were concentrated in vacuo. Purification on silica gel (PE: E A=I 0: 1) afforded 1.5 g of 3 (yield71percent).

References: [1]Patent: WO2010/94242,2010,A1 .Location in patent: Preparation III.2.

10
[ 42260-39-9 ]
[ 1187055-81-7 ]
[ 1241504-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;	To a solution 3 (prepared above) in 800 ml of dioxane were added K3PO4 (118 g, 0.561 mol), 2 chloro-4-phenylpyridine (35.5 g, 0.187 mol), and Pd(dppf)Cl2 (6 g, 5.6 mmol). The suspension was stirred at 80 0C overnight, filtered, and concentrated in vacuo. Purification on silica gel afforded 4 as a yellow solid (30 g, 64percent).

References: [1]Patent: WO2010/94242,2010,A1 .Location in patent: Preparation II.3.

11
[ 883874-56-4 ]
[ 42260-39-9 ]
2-{4-[4-(2-fluorophenyl)piperazin-1-yl]butyl}amino-4-phenylpyridine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5376 - 5379.

12
[ 42260-39-9 ]
[ 189061-44-7 ]
[ 883874-61-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5376 - 5379.

13
[ 42260-39-9 ]
[ 1335148-36-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5206 - 5209.

14
[ 42260-39-9 ]
C₁₈H₁₃ClN₂O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5206 - 5209.

15
[ 42260-39-9 ]
[ 214360-60-8 ]
[ 1351665-15-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5206 - 5209.

16
[ 73583-37-6 ]
[ 42260-39-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 595 - 603.

17
[ 73583-37-6 ]
[ 24388-23-6 ]
[ 42260-39-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 595 - 603.

18
[ 108-86-1 ]
[ 42260-39-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 595 - 603.

19
[ 108-86-1 ]
[ 458532-84-8 ]
[ 42260-39-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 595 - 603.

20
[ 6302-53-0 ]
[ 42260-39-9 ]
[ 1375748-16-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃;Inert atmosphere;	General procedure (0.5-3.0 mmol scale) for the preparation of compounds 2a-t: A thick-glass, screw-capped pressure tube (50 mL) was charged with a suspension of the starting imidazoline (1.0 equiv), heteroaryl halide (1.1 equiv) and Cs2CO3 (1.0-3.0 equiv, an additional equivalent per salt component of the reactants) in toluene (3 mL/mmol). Pd(OAc)2 (0.02 equiv) and BINAP (0.4 equiv) were weighed out into a vial, suspended in toluene (2 mL/mmol) and shaken in a 100 °C oil bath for 2 min. The resulting clear, purple catalyst solution was added in one portion to the vigorously stirred reaction mixture. The tube was filled with argon, capped, and stirred at 100 °C for 16-20 h. The mixture was cooled, and partitioned between EtOAc and H2O. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography on silica gel using an appropriate gradient of acetone in hexane (or MeOH in CH2Cl2) as eluent to provide the target product 2.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 2876 - 2880.

21
[ 42260-39-9 ]
[ 109152-85-4 ]
[ 1375748-07-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃;Inert atmosphere;	General procedure (0.5-3.0 mmol scale) for the preparation of compounds 2a-t: A thick-glass, screw-capped pressure tube (50 mL) was charged with a suspension of the starting imidazoline (1.0 equiv), heteroaryl halide (1.1 equiv) and Cs2CO3 (1.0-3.0 equiv, an additional equivalent per salt component of the reactants) in toluene (3 mL/mmol). Pd(OAc)2 (0.02 equiv) and BINAP (0.4 equiv) were weighed out into a vial, suspended in toluene (2 mL/mmol) and shaken in a 100 °C oil bath for 2 min. The resulting clear, purple catalyst solution was added in one portion to the vigorously stirred reaction mixture. The tube was filled with argon, capped, and stirred at 100 °C for 16-20 h. The mixture was cooled, and partitioned between EtOAc and H2O. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography on silica gel using an appropriate gradient of acetone in hexane (or MeOH in CH2Cl2) as eluent to provide the target product 2.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 2876 - 2880.

22
[ 14432-12-3 ]
[ 591-50-4 ]
[ 73183-34-3 ]
[ 42260-39-9 ]

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

23
[ 26452-80-2 ]
[ 98-80-6 ]
[ 57311-18-9 ]
[ 42260-39-9 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 7758 - 7763.

24
[ 26452-80-2 ]
[ 98-80-6 ]
[ 57311-18-9 ]
[ 26274-35-1 ]
[ 42260-39-9 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 7758 - 7763.

25
[ 153034-86-7 ]
[ 780-69-8 ]
[ 42260-39-9 ]
[ 53344-74-4 ]

References: [1]Organic Letters,2013,vol. 15,p. 5378 - 5381.

26
[ 153034-86-7 ]
[ 4406-77-3 ]
[ 42260-39-9 ]

References: [1]Organic Letters,2014,vol. 16,p. 1264 - 1267.

27
[ 42260-39-9 ]
[ 1609374-04-0 ]
[ 1609374-06-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In water; ethyl acetate; toluene;Inert atmosphere; Reflux;	2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (5.96 g, 19.28 mmol), <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> (4.39 g, 23.13 mmol),tris(dibenzylideneacetone)palladium(0) (0.353 g, 0.386 mmol) and 2-Dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (.8g, 1.951 mmol) were charged into a 500 mL 2-neck flask. Potassium phosphate tribasic (12.26 g, 57.8 mmol) was thendissolved in 45 mL of water. This solution was charged into the reaction mixture. The reaction mixture was degassedwith nitrogen then was heated to reflux overnight. The reaction mixture was cooled to room temperature. The toluenelayer was separated and was dried over magnesium sulfate. These organics were filtered and concentrated undervacuum. The crude product was passed through a silica gel column using 70-99percent toluene/ heptanes followed by 5-15percentethyl acetate/ toluene. Some of the impure product fractions were columned on silica gel using 5-15percent ethyl acetate/DCM. All the clean product fractions were combined yielding 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine(5.3 g, 15.76 mmol, 82 percent yield).
78%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux;	A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (4.34 g, 14.03 mmol), <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> (2.66 g,14.03 mmol), Pd2(dba)3 (0.257 g 0.281 mmol), dicyclohexyl(2?,6?-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine (0.582 g,1.42 mmol), potassium phosphate (8.93 g, 42.1 mmol), toluene (180 mL) and water (28 mL) was degassed with nitrogenand then refluxed overnight. The mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layerwas dried on Na2SO4 and then further purified by column chromatography using ethyl acetate in hexanes to give 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (3.66 g, 10.88 mmol, 78 percent yield).

References: [1]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0176; 0177.
[2]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0231.

28
[ 42260-39-9 ]
[ 1609374-07-3 ]