[ CAS No. 825-56-9 ] {[proInfo.proName]}

Name: 825-56-9|2-Phenyl-1,3,4-oxadiazole|95%
Brand: Ambeed
SKU: A225522
Price: 44.0 USD
Availability: InStock
Rating: 96 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 825-56-9

Structure of 825-56-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 825-56-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 825-56-9 ]

SDS Specification

Alternatived Products of [ 825-56-9 ]

Product Details of [ 825-56-9 ]

CAS No. :	825-56-9	MDL No. :	MFCD00491613
Formula :	C₈H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZEOMRHKTIYBETG-UHFFFAOYSA-N
M.W :	146.15	Pubchem ID :	13217
Synonyms :

Calculated chemistry of [ 825-56-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.73
TPSA :	38.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	1.31
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	1.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.25
Solubility :	0.831 mg/ml ; 0.00568 mol/l
Class :	Soluble
Log S (Ali) :	-1.73
Solubility :	2.73 mg/ml ; 0.0187 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.36
Solubility :	0.0636 mg/ml ; 0.000436 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.89

Safety of [ 825-56-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 825-56-9 ]

* 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.

Upstream synthesis route of [ 825-56-9 ]
Downstream synthetic route of [ 825-56-9 ]

[ 825-56-9 ] Synthesis Path-Upstream 1~3

1
[ 825-56-9 ]
[ 51039-53-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70 - -65℃; for 2 h; Inert atmosphere Stage #2: With bromine In tetrahydrofuran; hexane at -70 - -65℃; for 1 h;	To a 500 mL four neck flask was charged tetra hydrofuran (170 mL) and 4 (17.0 g, 0.1163 mol). The reactionmass was cooled to -65 to -70 °C under nitrogen atmospherewith stirring and added n-butyl lithium (60.66 mL, 2.3 M inn-hexane, 0.1395 mol) over a period of 1h, further reactionmass was stirred at same temperature for 1.0 h. Bromine(11.15 g, 0.1395 mol) was added slowly to reaction mass bymaintaining the reaction temperature -65 to -70 °C. Furtherstirred the reaction mass for 1.0 h. Reaction completion wasmonitored by TLC. Reaction mass was warmed to around -10 °C and quenched with 1.0 N HCl solution (100 mL). Reactionmass was warmed to room temperature, compoundwas extracted with ethyl acetate (2 x 100 mL). Combinedorganic layer was washed with water (1 x 100 mL) followedby brine (100 mL), dried over anhydrous sodium sulphateand concentrated to one volume stage. Compound was crystallizedusing petroleum ether to yield the title compound asoff white solid. (Yield: 24.3 g, 93 percent). 1H-NMR (400 MHz,DMSO-d6): δ 7.57-7.68 (m, 3H), 7.95-7.98 (m, 2H). MS(ESI) m/z: 226.0

Reference： [1] Letters in Drug Design and Discovery, 2013, vol. 10, # 8, p. 783 - 791

2
[ 825-56-9 ]
[ 3004-42-0 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 39, p. 8276 - 8279

3
[ 825-56-9 ]
[ 1483-31-4 ]

Reference： [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 1, p. 77 - 80

[ 825-56-9 ] Synthesis Path-Downstream 1~87

1
[ 613-94-5 ]
[ 149-73-5 ]
[ 825-56-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	toluene-4-sulfonic acid; for 0.5h;Heating / reflux;	Benzoic hydrazide (54.4 g, 400 mmol), p-toluenesulfonic acid monohydrate [(1.] [1 G,] 5.78 mmol), and [TRIMETHYLORTHOFORMATE] (66 mL, 600 mmol) were heated to reflux for 30 min. The reaction mixture was then vacuum distilled, with fractions boiling between 90C and 120C at 4 torr being combined to afford 2-phenyl- [[1,] 3,4] oxadiazole as a colorless liquid (44.4 g, 76%) which crystallized upon standing, [MP 34-36 C.]

Reference： [1]Monatshefte fur Chemie,2007,vol. 138,p. 1253 - 1255
[2]Patent: WO2004/14882,2004,A2 .Location in patent: Page 36
[3]Journal of Medicinal Chemistry,2001,vol. 44,p. 1268 - 1285
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2909 - 2914

2
[ 825-56-9 ]
[ 62-53-3 ]
[ 14331-64-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridinium trifluroacetate; at 110℃; for 0.333333h;	General procedure: A 25 ml flask was charged with oxadiazole (2 mmol), primary amine (2.2-4.0 mmol), and protic ionic liquid (2 g). The mixture was stirred at 110 C and monitored by TLC until oxadiazole was not detected unless otherwise stated. The reaction mixture was diluted with CH2Cl2 (15 ml), followed by washing twice with H2O (10 ml×2), from which protic ionic liquid could be recovered by rotavapor and recrystallization. The organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel with CH2Cl2/MeOH to give 1,2,4-triazole.

Reference： [1]Chemistry of Heterocyclic Compounds,2005,vol. 41,p. 866 - 871
[2]Tetrahedron,2012,vol. 68,p. 4813 - 4819
[3]Dalton Transactions,2019,vol. 48,p. 1892 - 1899
[4]Journal of Materials Chemistry C,2019,vol. 7,p. 2022 - 2028

3
[ 825-56-9 ]
[ 58521-45-2 ]
[ 660847-45-0 ]

Yield	Reaction Conditions	Operation in experiment
70%		A solution [OF 2-PHENYL- [1,] 3,4] oxadiazole (3.34g, 16.0 mmol) in anhydrous THF (100 mL) was cooled with a dry ice bath and maintained under an atmosphere of dry nitrogen. A solution of 1.6M n-butyllithium in hexanes (10.0 mL, 16.0 mmol) was added via syringe. After 1 [HR,] magnesium bromide diethyl etherate (4.13g, 16.0 mmol) was added in one portion. After another hr, a solution of freshly prepared [(1-] formyl-3-methylbutyl)-carbamic acid [TERT-BUTYL] ester (BOC-Leu-H, 1.94g, 8.0 mmol, prepared by the procedure described in Falkiewicz, [B.] et [AL.] Nucleosides and Nucleotides 20 1393, 2001) was added. After an additional 1.5 hr at low temperature, 1.0 N aqueous [HC1] was added and the cold bath was removed. Upon warming to room temperature the mixture was transferred to a separatory funnel and 100 ml diethyl ether was added. The organic phase was separated and the aqueous phase was extracted twice more with 50 mL portions of ether. The combined organic phase was washed with water, saturated sodium bicarbonate, and brine, then dried over anhydrous magnesium sulfate. Filtration and solvent evaporation gave an oily residue that was flash chromatographed on silica gel, eluting with a gradient of 25% to 50% ethyl acetate in hexane, to give [{L- [HYDROXY- (5-PHENYL- [L,] 3,4] oxadiazol-2-yl) methyl]- [3-METHYLBUTYL} CARBAMIC] acid [TERT-BUTYL] ester (1.61g, 70% yield).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2953 - 2968
[2]Patent: WO2004/14882,2004,A2 .Location in patent: Page 36-37

4
[ 73789-56-7 ]
[ 65-85-0 ]
[ 825-56-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	In dichloromethane; at 20℃; for 0.166667h;Sonication;	General procedure: To a solution of N-isocyanoiminotriphenylphosphorane (2) (0.302 g, 1 mmol) in dry CH2Cl2 (4 mL), a solution of 2-aryl-benzoic acid derivatives (1) (1 mmol) in dry CH2Cl2 (4 mL) was added and the mixture was sonicated in an ultrasonic cleaner at room temperature. The solvent was removed under reduced pressure, and the viscous residue was purified by precoated glass-backed plates [silica gel; petroleum ether/ethyl acetate (10:2)]. The solvent was removed under reduced pressure, and the product (5) was obtained.

Reference： [1]Ultrasonics Sonochemistry,2014,vol. 21,p. 262 - 267
[2]Tetrahedron Letters,2007,vol. 48,p. 1549 - 1551

5
[ 5798-75-4 ]
[ 88-65-3 ]
[ 825-56-9 ]
[ 19542-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In pyridine; methanol	5 Synthesis of Conducting Molecules Containing Phenyl-1,3,4-oxadiazole These compounds can be synthesised according to the following reaction scheme: Ethyl-4-bromobenzoate is treated with hydrazine monohydrate in methanol under reflux conditions to obtain product X, 4-bromobenzoic hydrazide. Reaction of compound X with bromobenzoic acid in pyridine at 120° C. gives product XI, bis-(4-bromophenyl) hydrazine. Compound XI is then treated with sulfonyl chloride to afford 2,5-bis-(4-bromophenyl)-1,3,4-oxadiazole (Compound XII), which is further reacted 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane under conditions similar to step-3 in Example 1. The resulting product thus obtained is subjected to Suzuki coupling conditions similar to step-5 in Example 1 to obtain the desired product XIII. Other alligator clips which can be introduced are CN, SCN, NH2, pyridine.

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US2007/215866, 2007, A1

6
[ 825-56-9 ]
[ 2697-71-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,10-Phenanthroline; iodine; copper(ll) bromide; lithium tert-butoxide; In 1,4-dioxane; at 60℃;Inert atmosphere;	General procedure: To a flame-dried reaction tube was added 1,3-azoles (0.5 mmol, 1.0 eq), 1,10-phenoline (0.5 mmol, 1.0 eq), LiOtBu (1.0mmol, 2.0 eq), CuBr2 (0.05 mmol, 0.1 eq) and iodine (0.75 mmol, 1.5eq). Dry 1,4-dioxane (2 mL) was added to the mixture and the mixture was heated to 60C by putting the reaction tube to a preheated oil bath until the products were not increased. The mixture was cooled to room temperature and filtered through a short pad of silica gel. The silica gel was washed with EtOAc (20 mL) and the combined the organic phase was concentrated under reduced pressure to give a residue which was purified by silica gel column chromatography to afford the iodination product.

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7685 - 7688
[2]Tetrahedron Letters,2015,vol. 56,p. 511 - 513
[3]European Journal of Organic Chemistry,2015,vol. 2015,p. 77 - 80

7
[ 825-56-9 ]
[ 153371-25-6 ]
[ 639519-90-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of the 2-phenyl-[1.3.4]oxadiazole (10 g, 68.5 mmol) in THF (100mL) was added «-BuLi (1 .6 M solution in 42.8 mL of hexane) dropwise under N2 at -78 C.After 1 h, MgBr.Et2O (17.69 g, 68.5 mmol) was added and the reaction mixture was allowed towarm to -45 C for 1 h before being treated with (S)-2-.5oc~aminobutyraaldehyde (7.8 g, 41mmol) in THF (20 mL). The reaction mixture was stirred for 1 h, quenched with saturatedNKUCl, and extracted with ethyl acetate. The organic layer was washed with brine, dried withMgSC>4 and concentrated: The residue was purified by silica gel column chromatography toyield2-(2(iS)-50c-amino-l-hydroxybutyl)-5-phenyl-[1.3.4]-oxadiazole (9.7g).
		Step 2 To a stirred solution of the 2-phenyl-[1, 3,4] oxadiazole (10 g, 68.5 mmol) in THF (100 mL) was added N-BULI (1.6 M solution in 42.8 mL of hexane) dropwise under N2 AT-78 C. After 1 h, MgBr. Et2O (17.69 g, 68.5 mmol) was added and the reaction mixture was allowed to warm to-45 C for 1 h before being treated with 2 (S)-Boc-aminobutyraaldehyde (7.8 g, 41 mmol) in THF (20 mL). The reaction mixture was stirred for 1 h, quenched with saturated NH4CI, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04 and concentrated. The residue was purified by silica gel column chromatography to yield 2-(2(S)--Boc-amino-1-hydroxybutyl)-5-phenyl-1, 3,4-oxadiazole (9.7g).
		To a stirred solution of the 2-phenyl- [1. 3.4] oxadiazole (10 g, 68.5 mmol) in THF (100 mL) was added n-BuLi (1.6 M solution in 42.8 mL of hexane) dropwise under N2 at-78 C.After 1 h, MgBr. Et2O (17.69 g, 68.5 mmol) was added and the reaction mixture was allowed to warm to-45 C for 1 h before being treated with 2 (S)-Boc-aminobutyraldehyde (7.8 g, 41 mmol) in THE (20 mL). The reaction mixture was stirred for 1 h, quenched with saturated NH4C1, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and concentrated. The residue was purified by silica gel column chromatography to yield 2-[2 (O-Boc-amino-1-hydroxybutyl]-5-phenyl-[l,. 3.4]-oxadiazole (9.7 g).

		Reference Q Synthesis of [(S)-2-AMINO-1- (5-PHENYL- [1,] 3,4] [OXADIAZOL-2-YL)-1-BUTAN-1-OL] Step 1 A mixture of the benzoic hydrazide (22.5 g, 165 mmol), [TRIETHYLORTHOFORMATE] (150 [ML)] and p-toluenesulfonic acid (300 mg) was heated at [120 C] for 12 h. Excess [TRIETHYLORTHOFORMATE] was removed under vacuum and the residue was purified by silica gel column chromatography to produce [2-PHENYL- [1,] 3,4]-oxadiazole (14.5 g). Step 2 To a stirred solution of the [2-PHENYL- [1,] 3,4] oxadiazole (10 g, 68.5 mmol) in THF (100 [MLA] was added n-BuLi [(1.] 6 M solution in 42.8 [ML OF HEXANE) DROPWISE UNDER N2 AT-78 C.] After 1 h, MgBr. Et2O (17.69 g, 68.5 mmol) was added and the reaction mixture was allowed to warm to-45 C for 1 h before being treated with [(S)-2-BOC-AMINOBUTYRA-ALDEHYDE] (7.8 g, 41 mmol) in THF (20 mL). The reaction mixture was stirred for 1 h, quenched with saturated [NH4C1,] and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04 and concentrated. The residue was purified by silica gel column chromatography to yield [2- ( (S)-2-BOE-AMINO-L-HYDROXYBUTYL)-5-PHENYL- [1,] 3,4]-oxadiazole (9. [7 G).] Step 3 [2- ( ()-2-BOC-AMINO-L-HYDROXYBUTYL)-5-PHENYL- [1,] 3,4]-oxadiazole (505 mg, [1.] 5 mmol) and MeCl2 (5 mL) were mixed and TFA (1 mL) was added at room temperature. After stirring for 1 h, the solvent and excess TFA were removed under vacuum to produce 530 mg of [(S)-2-AMINO-L- (5-PHENYL- [1,] 3,4] oxadiazol-2-yl)-1-butanol TFA salt.
		To a stirred solution of the 2-phenyl- [1, 3,4] oxadiazole (10 g, 68.5 mmol) in THF (100 ml) was added n-BuLi (1.6 M solution in 42. 8 ml of hexane) dropwise under N2 at-78 C. After 1 h, MgBr. Et20 (17.69 g, 68.5 mmol) was added and the reaction mixture was allowed to warm to-45 C for 1 h before being treated with (S)-2-Boc-aminobutyraaldehyde (7.8 g, 41 mmol) in THF (20 ml). The reaction mixture was stirred for 1 h, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04 and concentrated. The residue was purified by silica gel column chromatography to yield 2- ( (S)-2-Boc-amino-1-hydroxybutyl)-5-phenyl- [1, 3,4]-oxadiazole (9.7 g).

Reference： [1]Patent: WO2004/108661,2004,A1 .Location in patent: Page/Page column 52
[2]Patent: WO2005/28454,2005,A1 .Location in patent: Page/Page column 54
[3]Patent: WO2005/63742,2005,A2 .Location in patent: Page/Page column 24
[4]Patent: WO2004/838,2003,A1 .Location in patent: Page 74-75
[5]Patent: WO2005/74904,2005,A2 .Location in patent: Page/Page column 59

8
[ 825-56-9 ]
[ 591-50-4 ]
[ 725-12-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper; potassium carbonate; at 120℃; for 12h;Inert atmosphere;	General procedure: Copperpowder (0.2 equiv) and K2CO3 (2.5 equiv) were added to asolution of 3,4-diaryl-1,2,4-triazole (1)or 2-aryl-1,3,4-oxadiazole (4) (1.0equiv) and iodobenzene (2) (1.2equiv) in PEG-400 (5 vol.). The reaction mixture was stirred at 120 oCunder nitrogen atmosphere for 12 h. After completion of the reaction asindicated by TLC, the reaction mixture was cooled to room temperature andpartitioned between water and ethyl acetate. The organic and aqueous layerswere then separated and aqueous layer was extracted with ethyl acetate twice.The combined organic extracts were dried over anhydrous sodiumsulfate and concentrated under reduced pressure to affordthe crude compound. The crude was further purified by silica gel chromatographyusing EtOAc/hexane aseluents to furnish the desired product 3or 5.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 690 - 692
[2]Organic Letters,2009,vol. 11,p. 3072 - 3075
[3]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3986 - 3990

9
[ 825-56-9 ]
[ 589-87-7 ]
[ 21510-43-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In dimethyl sulfoxide at 100℃; for 4h; Inert atmosphere;

Reference： [1]Kawano, Tsuyoshi; Yoshizumi, Tomoki; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Organic Letters, 2009, vol. 11, # 14, p. 3072 - 3075]

10
[ 825-56-9 ]
[ 932-87-6 ]
[ 1025371-32-7 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 9553 - 9556
[2]Journal of Organic Chemistry,2010,vol. 75,p. 1764 - 1766
[3]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3986 - 3990

11
[ 825-56-9 ]
[ 2996-92-1 ]
[ 725-12-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	With [2,2]bipyridinyl; copper (II)-fluoride; nickel(II) bromide diethylene glycol dimethyl ether; cesium fluoride In N,N-dimethyl acetamide at 150℃; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Hachiya, Hitoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Angewandte Chemie - International Edition, 2010, vol. 49, # 12, p. 2202 - 2205]

12
[ 825-56-9 ]
[ 91703-34-3 ]
[ 94138-70-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis-triphenylphosphine-palladium(II) chloride; copper(I) bromide; sodium t-butanolate; In toluene; at 100℃; for 10h;Inert atmosphere;	Under the nitrogen atmosphere, an over-dried Schlenk tube with a magnetic stirring bar was charged with 2-(gem-dibromovinyl)phenol or 2-(gem-dibromovinyl)aniline (0.50 mmol), azole (0.50 mmol), CuBr (0.05 mmol), Pd(PPh3)2Cl2 (0.025 mmol), LiOtBu (2.0 mmol), and toluene (2.0 mL). The reaction vessel was placed in an oil bath at 100 C and the mixture was stirred for 10 h, then it was cooled to room temperature. The solvent was filtered and concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate) to give the corresponding benzofuranyl or indolyl azole product.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5913 - 5919
[2]Chemical Communications,2011,vol. 47,p. 5611 - 5613

13
[ 825-56-9 ]
[ 95186-48-4 ]
[ 1321985-66-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With bis-triphenylphosphine-palladium(II) chloride; copper(I) bromide; sodium t-butanolate; In toluene; at 100℃; for 10h;Inert atmosphere;	Under the nitrogen atmosphere, an over-dried Schlenk tube with a magnetic stirring bar was charged with 2-(gem-dibromovinyl)phenol or 2-(gem-dibromovinyl)aniline (0.50 mmol), azole (0.50 mmol), CuBr (0.05 mmol), Pd(PPh3)2Cl2 (0.025 mmol), LiOtBu (2.0 mmol), and toluene (2.0 mL). The reaction vessel was placed in an oil bath at 100 C and the mixture was stirred for 10 h, then it was cooled to room temperature. The solvent was filtered and concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate) to give the corresponding benzofuranyl or indolyl azole product.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5913 - 5919

14
[ 825-56-9 ]
[ 167558-54-5 ]
[ 37574-83-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis-triphenylphosphine-palladium(II) chloride; copper(I) bromide; sodium t-butanolate; In toluene; at 100℃; for 10h;Inert atmosphere;	Under the nitrogen atmosphere, an over-dried Schlenk tube with a magnetic stirring bar was charged with 2-(gem-dibromovinyl)phenol or 2-(gem-dibromovinyl)aniline (0.50 mmol), azole (0.50 mmol), CuBr (0.05 mmol), Pd(PPh3)2Cl2 (0.025 mmol), LiOtBu (2.0 mmol), and toluene (2.0 mL). The reaction vessel was placed in an oil bath at 100 C and the mixture was stirred for 10 h, then it was cooled to room temperature. The solvent was filtered and concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate) to give the corresponding benzofuranyl or indolyl azole product.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5913 - 5919

15
[ 825-56-9 ]
[ 588-72-7 ]
[ 1874-31-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper(l) iodide; lithium tert-butoxide; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 70℃; for 3h;Inert atmosphere;	General procedure: In a 10 mL round bottom flask under nitrogen atmosphere, CuI (9 mg, 0.05 mmol), DMEDA (4.5 mg, 0.05 mmol), LiO-t-Bu (80 mg, 1.0 mmol), 2-aryl-1,3,4-oxadiazole (0.50 mmol), and trans-beta-iodostyrene (0.50 mmol) in DMSO (2.0 mL) were taken. The reaction mixture was stirred at 70 C for 3 h. The progress of the reaction was monitored by TLC. After the consumption of the starting materials, the reaction mixture was allowed to cool, and subsequently extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 3 in 85-93% yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 300 - 305
[2]Journal of Organic Chemistry,2011,vol. 76,p. 9542 - 9547

16
[ 825-56-9 ]
[ 1059544-14-7 ]
[ 1350920-02-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(l) iodide; lithium tert-butoxide; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 70℃; for 3h;Inert atmosphere;	General procedure: In a 10 mL round bottom flask under nitrogen atmosphere, CuI (9 mg, 0.05 mmol), DMEDA (4.5 mg, 0.05 mmol), LiO-t-Bu (80 mg, 1.0 mmol), 2-aryl-1,3,4-oxadiazole (0.50 mmol), and trans-beta-iodostyrene (0.50 mmol) in DMSO (2.0 mL) were taken. The reaction mixture was stirred at 70 C for 3 h. The progress of the reaction was monitored by TLC. After the consumption of the starting materials, the reaction mixture was allowed to cool, and subsequently extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 3 in 85-93% yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 300 - 305

17
[ 825-56-9 ]
[ 1174153-19-5 ]
[ 1350919-96-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; lithium tert-butoxide; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 70℃; for 3h;Inert atmosphere;	General procedure: In a 10 mL round bottom flask under nitrogen atmosphere, CuI (9 mg, 0.05 mmol), DMEDA (4.5 mg, 0.05 mmol), LiO-t-Bu (80 mg, 1.0 mmol), 2-aryl-1,3,4-oxadiazole (0.50 mmol), and trans-beta-iodostyrene (0.50 mmol) in DMSO (2.0 mL) were taken. The reaction mixture was stirred at 70 C for 3 h. The progress of the reaction was monitored by TLC. After the consumption of the starting materials, the reaction mixture was allowed to cool, and subsequently extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 3 in 85-93% yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 300 - 305

18
[ 825-56-9 ]
[ 1350920-08-9 ]
[ 1350920-05-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; lithium tert-butoxide; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 70℃; for 3h;Inert atmosphere;	General procedure: In a 10 mL round bottom flask under nitrogen atmosphere, CuI (9 mg, 0.05 mmol), DMEDA (4.5 mg, 0.05 mmol), LiO-t-Bu (80 mg, 1.0 mmol), 2-aryl-1,3,4-oxadiazole (0.50 mmol), and trans-beta-iodostyrene (0.50 mmol) in DMSO (2.0 mL) were taken. The reaction mixture was stirred at 70 C for 3 h. The progress of the reaction was monitored by TLC. After the consumption of the starting materials, the reaction mixture was allowed to cool, and subsequently extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 3 in 85-93% yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 300 - 305

19
[ 825-56-9 ]
[ 42599-24-6 ]
[ 1874-31-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; lithium tert-butoxide; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 70℃; for 3h;Inert atmosphere;	General procedure: In a 10 mL round bottom flask under nitrogen atmosphere, CuI (9 mg, 0.05 mmol), DMEDA (4.5 mg, 0.05 mmol), LiO-t-Bu (80 mg, 1.0 mmol), 2-aryl-1,3,4-oxadiazole (0.50 mmol), and trans-beta-iodostyrene (0.50 mmol) in DMSO (2.0 mL) were taken. The reaction mixture was stirred at 70 C for 3 h. The progress of the reaction was monitored by TLC. After the consumption of the starting materials, the reaction mixture was allowed to cool, and subsequently extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 3 in 85-93% yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 300 - 305

20
[ 825-56-9 ]
[ 69731-27-7 ]
[ 1350920-02-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With copper(l) iodide; lithium tert-butoxide; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 70℃; for 3h;Inert atmosphere;	General procedure: In a 10 mL round bottom flask under nitrogen atmosphere, CuI (9 mg, 0.05 mmol), DMEDA (4.5 mg, 0.05 mmol), LiO-t-Bu (80 mg, 1.0 mmol), 2-aryl-1,3,4-oxadiazole (0.50 mmol), and trans-beta-iodostyrene (0.50 mmol) in DMSO (2.0 mL) were taken. The reaction mixture was stirred at 70 C for 3 h. The progress of the reaction was monitored by TLC. After the consumption of the starting materials, the reaction mixture was allowed to cool, and subsequently extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 3 in 85-93% yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 300 - 305

21
[ 825-56-9 ]
[ 124643-45-4 ]
[ 1354644-44-2 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 664 - 667

22
[ 825-56-9 ]
[ 157869-15-3 ]
[ 1354644-46-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 664 - 667

23
[ 825-56-9 ]
[ 221910-19-6 ]
[ 1354644-48-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 664 - 667

24
[ 825-56-9 ]
[ 824-79-3 ]
[ 1874-47-1 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: Under nitrogen atmosphere, a sealable reaction tube equipped with a magnetic stirrer bar was charged with azole (0.50 mmol), sodium arylsulfinate (1.0 mmol), Pd(OAc)2 (0.025 mmol), Cu(OAc)2 (1.0 mmol), CF3COOH (0.50 mmol), and dimethylglycol (2.0 mL). The rubber septum was then replaced by a Teflon-coated screw cap, and the reaction vessel placed in an oil bath at 120 C for 24 h. After the reaction was completed, it was cooled to room temperature and the mixture was treated with K2CO3 solution (1.0 mol/L, 3.0 mL), then extracted with ethyl acetate. The resulting solution was dried by Na2SO4 then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate=12:1, v/v) to give the desired product.

Reference： [1]Tetrahedron,2012,vol. 68,p. 1926 - 1930

25
[ 504-30-3 ]
[ 825-56-9 ]
[ 1366397-77-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1854 - 1857

26
[ 825-56-9 ]
[ 24544-04-5 ]
[ 1380492-44-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridinium trifluroacetate; at 110℃; for 0.333333h;	General procedure: A 25 ml flask was charged with oxadiazole (2 mmol), primary amine (2.2-4.0 mmol), and protic ionic liquid (2 g). The mixture was stirred at 110 C and monitored by TLC until oxadiazole was not detected unless otherwise stated. The reaction mixture was diluted with CH2Cl2 (15 ml), followed by washing twice with H2O (10 ml×2), from which protic ionic liquid could be recovered by rotavapor and recrystallization. The organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel with CH2Cl2/MeOH to give 1,2,4-triazole.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4813 - 4819
[2]Organometallics,2015,vol. 34,p. 3665 - 3669
[3]Dalton Transactions,2014,vol. 43,p. 16227 - 16237

27
[ 825-56-9 ]
[ 104-94-9 ]
[ 70208-16-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With pyridinium trifluroacetate; at 110℃; for 0.333333h;	General procedure: A 25 ml flask was charged with oxadiazole (2 mmol), primary amine (2.2-4.0 mmol), and protic ionic liquid (2 g). The mixture was stirred at 110 C and monitored by TLC until oxadiazole was not detected unless otherwise stated. The reaction mixture was diluted with CH2Cl2 (15 ml), followed by washing twice with H2O (10 ml×2), from which protic ionic liquid could be recovered by rotavapor and recrystallization. The organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel with CH2Cl2/MeOH to give 1,2,4-triazole.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4813 - 4819

28
[ 825-56-9 ]
[ 109-73-9 ]
[ 1380492-58-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridinium acetate; at 110℃; for 2h;	General procedure: A 25 ml flask was charged with oxadiazole (2 mmol), primary amine (2.2-4.0 mmol), and protic ionic liquid (2 g). The mixture was stirred at 110 C and monitored by TLC until oxadiazole was not detected unless otherwise stated. The reaction mixture was diluted with CH2Cl2 (15 ml), followed by washing twice with H2O (10 ml×2), from which protic ionic liquid could be recovered by rotavapor and recrystallization. The organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel with CH2Cl2/MeOH to give 1,2,4-triazole.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4813 - 4819

29
[ 825-56-9 ]
[ 88-05-1 ]
[ 1380492-43-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridinium trifluroacetate; at 110℃; for 0.333333h;	General procedure: A 25 ml flask was charged with oxadiazole (2 mmol), primary amine (2.2-4.0 mmol), and protic ionic liquid (2 g). The mixture was stirred at 110 C and monitored by TLC until oxadiazole was not detected unless otherwise stated. The reaction mixture was diluted with CH2Cl2 (15 ml), followed by washing twice with H2O (10 ml×2), from which protic ionic liquid could be recovered by rotavapor and recrystallization. The organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel with CH2Cl2/MeOH to give 1,2,4-triazole.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4813 - 4819
[2]Dalton Transactions,2014,vol. 43,p. 16227 - 16237

30
[ 825-56-9 ]
[ 13922-41-3 ]
[ 897-18-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With [2,2]bipyridinyl; potassium phosphate; copper diacetate; palladium diacetate; In dimethyl sulfoxide; at 100℃; for 12h;	General procedure: In a 10 mL round bottom flask Pd(OAc)2 (5 mol %, 11 mg), Cu(OAc)2 (10 mol %, 20 mg), 2,2?-bipyridine (30 mol %, 44 mg) and K3PO4 (1.5 mmol, 318.3 mg), aryl boronic acid (1.3 mmol), and 2-aryl 1,3,4-oxadiazole (1.0 mmol)were added to a solution of DMSO (2.5 mL) under air. The reaction mixture was stirred for 10 min at room temperature then heated at 100 C for 12 h. The progress of the reaction was monitored by TLC. After consumption of starting material the reaction mixture was allowed to cool and subsequently extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 5 in 83-92% yield.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2220 - 2225

31
[ 6165-69-1 ]
[ 825-56-9 ]
[ 1146542-70-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With [2,2]bipyridinyl; potassium phosphate; copper diacetate; palladium diacetate; In dimethyl sulfoxide; at 100℃; for 12h;	General procedure: In a 10 mL round bottom flask Pd(OAc)2 (5 mol %, 11 mg), Cu(OAc)2 (10 mol %, 20 mg), 2,2?-bipyridine (30 mol %, 44 mg) and K3PO4 (1.5 mmol, 318.3 mg), aryl boronic acid (1.3 mmol), and 2-aryl 1,3,4-oxadiazole (1.0 mmol)were added to a solution of DMSO (2.5 mL) under air. The reaction mixture was stirred for 10 min at room temperature then heated at 100 C for 12 h. The progress of the reaction was monitored by TLC. After consumption of starting material the reaction mixture was allowed to cool and subsequently extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4. Concentration in vacuo followed by column chromatography (EtOAc/hexane: 5:95 to 10:90) gave pure compound 5 in 83-92% yield.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2220 - 2225

32
[ 825-56-9 ]
[ 110-96-3 ]
[ 2043-61-0 ]
N-(cyclohexyl(5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-N-isobutyl-2-methylpropan-1-amine [ No CAS ]