[ CAS No. 70886-33-8 ] {[proInfo.proName]}

Name: 70886-33-8|5-Nitrobenzoxazole|98%
Brand: Ambeed
SKU: A848571
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Quality Control of [ 70886-33-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 70886-33-8 ]

SDS Specification

Alternatived Products of [ 70886-33-8 ]

Product Details of [ 70886-33-8 ]

CAS No. :	70886-33-8	MDL No. :	MFCD01359855
Formula :	C₇H₄N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MNEOLRFGVQZMLA-UHFFFAOYSA-N
M.W :	164.12	Pubchem ID :	1482180
Synonyms :

Calculated chemistry of [ 70886-33-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.83
TPSA :	71.85 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	1.42
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	0.71
Log Po/w (SILICOS-IT) :	-0.29
Consensus Log Po/w :	0.99

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	0.942 mg/ml ; 0.00574 mol/l
Class :	Soluble
Log S (Ali) :	-2.53
Solubility :	0.48 mg/ml ; 0.00293 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.29
Solubility :	0.849 mg/ml ; 0.00518 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.39

Safety of [ 70886-33-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 70886-33-8 ]

* 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 [ 70886-33-8 ]
Downstream synthetic route of [ 70886-33-8 ]

[ 70886-33-8 ] Synthesis Path-Upstream 1~6

1
[ 273-53-0 ]
[ 17200-30-5 ]
[ 70886-33-8 ]

Reference： [1] Yakugaku Zasshi, 1953, vol. 73, p. 1316[2] Chem.Abstr., 1955, p. 299

2
[ 122-51-0 ]
[ 99-57-0 ]
[ 70886-33-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 150℃; for 6 h;	General procedure: A 50-mL, one-necked, round bottomed flask equipped with a magnetic stir bar was charged with the corresponding 2-aminophenol derivative (5.0 mmol, 1.0 equiv) and triethyl orthoformate (60.0 mmol, 12.0 equiv). The reaction mixture was carefully heated to 150 °C for 6 h. Upon completion, the reaction mixture was cooled to room temperature and the excess orthoformate and ethanol byproduct were removed from the residue under reduced pressure. The crude product was further purified by silica gel (SiO₂) column chromatography to yield the desired substituted benzoxazole (Table S-2).
84%	With tungstate sulfuric acid In neat (no solvent) at 80 - 90℃; for 0.166667 h;	General procedure: To a mixture of orthoester (1.1 mmol) and o-aminophenol or o-aminothiophenol (1 mmol) was added TSA (1 molpercent). The mixture was stirred at 80–90 °C for the appropriate time according to Table 4. After the completion of the reaction (as indicated by TLC), the mixture was diluted with chloroform (10 mL) and the catalyst was separated by filtration. Further purification was achieved by column chromatography
76%	for 4 h; Reflux	General procedure: A mixture of 2-aminophenol derivative (5 mmol) and triethyl orthoformate (15 mL) was heated at reflux for 4 h. After cooling to room temperature, remained triethyl orthoformate was removed under reduced pressure and the residue was purified by column chromatography on silica gel.

Reference： [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 48, p. 11511 - 11515
[2] Journal of the Chinese Chemical Society, 2015, vol. 62, # 5, p. 412 - 419
[3] Tetrahedron, 2013, vol. 69, # 32, p. 6627 - 6633
[4] Comptes Rendus Chimie, 2013, vol. 16, # 11, p. 1029 - 1034
[5] Angewandte Chemie - International Edition, 2009, vol. 48, # 48, p. 9127 - 9130
[6] Chemistry - A European Journal, 2011, vol. 17, # 30, p. 8294 - 8298
[7] Tetrahedron Letters, 2012, vol. 53, # 34, p. 4588 - 4590
[8] Green Chemistry, 2013, vol. 15, # 9, p. 2365 - 2368
[9] Organic Preparations and Procedures International, 2013, vol. 45, # 1, p. 57 - 65
[10] Organic Letters, 2011, vol. 13, # 3, p. 522 - 525
[11] Journal of Molecular Catalysis A: Chemical, 2010, vol. 328, # 1-2, p. 119 - 123
[12] Angewandte Chemie - International Edition, 2012, vol. 51, # 28, p. 6993 - 6997
[13] Angewandte Chemie - International Edition, 2013, vol. 52, # 16, p. 4457 - 4461[14] Angew. Chem., 2013, vol. 125, # 16, p. 4553 - 4557,5

3
[ 99-57-0 ]
[ 149-73-5 ]
[ 70886-33-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	for 12 h; Reflux	A solution of 2-amino-4-nitrophenol (600 mg, 3.9 mmol) in trimethyl orthoformate (30 ml)was stirred at reflux for 12 hours_ The reaction mixture was slowly poured into ice-coldwater (100 ml)and extractedwith ethyl acetate (100 ml). The organiclayer was concentrated under reduced pressureand the residue 10 was purified by silica gel column chromatography eluting with dichloromethane: methanol=301to afford 5-nitrobenzo[d]oxazole as a white solid (530 mg, 83percent).LCMS (ESI):mlz = 164.0 [M+H(

Reference： [1] Patent: WO2015/154023, 2015, A1, . Location in patent: Page/Page column 228; 229
[2] Journal of Molecular Catalysis A: Chemical, 2010, vol. 328, # 1-2, p. 119 - 123

4
[ 99-57-0 ]
[ 70886-33-8 ]

Reference： [1] Patent: US2003/195201, 2003, A1,

5
[ 70886-35-0 ]
[ 70886-33-8 ]

Reference： [1] Journal of the Chemical Society, 1954, p. 2256,2257

6
[ 273-53-0 ]
[ 17200-30-5 ]
[ 70886-33-8 ]

Reference： [1] Yakugaku Zasshi, 1953, vol. 73, p. 1316[2] Chem.Abstr., 1955, p. 299

[ 70886-33-8 ] Synthesis Path-Downstream 1~80

1
[ 273-53-0 ]
[ 17200-30-5 ]
[ 70886-33-8 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1953,vol. 73,p. 1316
Chem.Abstr.,1955,p. 299

2
[ 70886-35-0 ]
[ 70886-33-8 ]

Reference： [1]Journal of the Chemical Society,1954,p. 2256,2257

3
[ 70886-33-8 ]
[ 70886-35-0 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 7277 - 7286

4
[ 70886-33-8 ]
[ 63837-12-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 5%-palladium/activated carbon; hydrogen; In methanol; at 20℃; for 12h;	To a solutionof <strong>[70886-33-8]5-nitro<strong>[70886-33-8]benzo[d]oxazole</strong></strong> (530 mg, 3.23 mmol) in methanol (30 ml)was added palladium on carbon (100 mg, dry, 5%). The mixture was stirred under a hydrogengas atmosphere at roomtemperature for 12 hours. The catalyst was removed by filtration and the filtratewas concentrated to dryness under reduced pressureto afford benzo[d]oxazol-5-amine as a yellow solid (430 mg, 100%).20 LCMS (ESI): m/z = 134.1 [M+Ht
66%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 12h;	A mixture of <strong>[70886-33-8]5-nitro<strong>[70886-33-8]benzo[d]oxazole</strong></strong> (13.0 g, 79 mmol) and 10% Pd/C (1.3 g) in methanol (200 mL) was stirred at RT for 12 h, under hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography (hexane/EtOAc=2/1) to afford benzo[d]oxazol-5-amine as a brown solid (7.0 g, 66%). LC/MS (ES+): m/z calculated for C7H6N2O: 134.1; found: 135.1 [M+H]. 1H NMR (400 MHz, CDCl3): delta 7.99 (s, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.05 (d, J=2.4 Hz, 1H), 6.75-6.72 (dd, J=8.6 Hz, 2.2 Hz, 1H), 3.72 (br, 2H).
66%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 12h;	Step 2: A mixture of <strong>[70886-33-8]5-nitro<strong>[70886-33-8]benzo[d]oxazole</strong></strong> (13.0 g, 79 mmol) and 10% Pd/C (1.3 g) in methanol (200 mL) was stirred at RT for 12 h. under hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography (hexane/EtOAc = 2/1) to afford benzo[d]oxazol-5-amine as a brown solid (7.0 g, 66%). LC/MS (ES+): m/z calculated for C7H6N2O: 134.1; found: 135.1 [M+H] NMR (400 MHz, CDCb): d 7.99 (s, 1H), 7.35 (d, j= 8.4 Hz, 1H), 7.05 (d, j= 2.4 Hz, 1H), 6.75-6.72 (dd, j= 8.6 Hz, 2.2 Hz, 1H), 3.72 (br, 2H).

Reference： [1]Patent: WO2015/154023,2015,A1 .Location in patent: Page/Page column 228; 229
[2]RSC Advances,2014,vol. 4,p. 22567 - 22574
[3]Patent: WO2020/36574,2020,A1 .Location in patent: Page/Page column 70
[4]Patent: US2020/55871,2020,A1 .Location in patent: Paragraph 0490
[5]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275
[6]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380

5
[ 70886-33-8 ]
[ 39835-09-1 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8197 - 8205

6
[ 591-50-4 ]
[ 70886-33-8 ]
[ 891-43-0 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 5824 - 5825

7
[ 70886-33-8 ]
3-(Benzooxazol-5-ylaminomethylene)-pentane-2,4-dione [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380

8
[ 70886-33-8 ]
8-Acetyl-6H-oxazolo[4,5-f]quinolin-9-one [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380

9
[ 70886-33-8 ]
7-Acetyl-5H-oxazolo[5,4-g]quinolin-8-one [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380

10
[ 70886-33-8 ]
2-[1-(Benzooxazol-5-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380

11
[ 70886-33-8 ]
8-Oxo-5,8-dihydro-oxazolo[5,4-g]quinoline-7-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275

12
[ 70886-33-8 ]
9-Oxo-6,9-dihydro-oxazolo[4,5-f]quinoline-8-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275

13
[ 70886-33-8 ]
[ 177492-53-4 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275

14
[ 99-57-0 ]
[ 70886-33-8 ]

Yield	Reaction Conditions	Operation in experiment
	With p-toluenesulfonic acid monohydrate; trimethyl orthoformate;	(a) 5-Nitrobenzoxazole. Following the procedure of A. R. Katritzky et al. Heterocycles 1995, 41, 345, to a round-bottomed flask was added 2-amino-4-nitrophenol (5.0 g, 32 mmol, Aldrich), trimethyl orthoformate (20 mL, 180 mmol, Aldrich) and p-toluenesulfonic acid monohydrate (300 mg, 1.6 mmol, Aldrich). The reaction mixture was magnetically stirred in a 95 C. oil bath for 1 h, and then allowed to cool to 25 C. The mixture was cooled to 0 C. to provide a precipitate which was collected by filtration, washed with cold toluene, pentane, then dried in vacuo to afford the title product as a dark brown powder.

Reference： [1]Patent: US2003/195201,2003,A1

15
[ 70886-33-8 ]
[ 68-12-2 ]
N,N-dimethyl-5-nitro-1,3-benzoxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; acetic acid; In water; 1,2-dichloro-ethane; at 90℃; for 12h;Green chemistry;	Benzoxazole (1.0 mmol), N,N-disubstituted formamide (15 mmol), TBAI (0.2 equiv/74 mg), TBHP (70% aqueous solution, 10 mmol/1.37 mL), and acetic acid (5.0 equiv) in 1,2-dichloroethane (3.0 mL) were added to a reaction vessel in air. The reaction mixture was heated in an oil bath at 90 C for 12 h. After completion of the reaction, the mixture was quenched by addition of a saturated solution of sodium disulfite (4.0 mL, for removal of excess TBHP) and a saturated solution of sodium hydrogen carbonate (4.0 mL). Then the mixture was extracted with ethyl acetate (3 × 15 mL), combined organic phases were dried over anhydrous Na2SO4 and the organic solvent was removed under vacuum. The crude residue was purified by chromatography on a silica gel column affording the desired product.

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 9127 - 9130
[2]Tetrahedron Letters,2014,vol. 55,p. 2233 - 2237

16
[ 122-51-0 ]
[ 99-57-0 ]
[ 70886-33-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 150℃; for 6h;	General procedure: A 50-mL, one-necked, round bottomed flask equipped with a magnetic stir bar was charged with the corresponding 2-aminophenol derivative (5.0 mmol, 1.0 equiv) and triethyl orthoformate (60.0 mmol, 12.0 equiv). The reaction mixture was carefully heated to 150 C for 6 h. Upon completion, the reaction mixture was cooled to room temperature and the excess orthoformate and ethanol byproduct were removed from the residue under reduced pressure. The crude product was further purified by silica gel (SiO2) column chromatography to yield the desired substituted benzoxazole (Table S-2).
84%	With tungstate sulfuric acid; In neat (no solvent); at 80 - 90℃; for 0.166667h;	General procedure: To a mixture of orthoester (1.1 mmol) and o-aminophenol or o-aminothiophenol (1 mmol) was added TSA (1 mol%). The mixture was stirred at 80-90 C for the appropriate time according to Table 4. After the completion of the reaction (as indicated by TLC), the mixture was diluted with chloroform (10 mL) and the catalyst was separated by filtration. Further purification was achieved by column chromatography
76%	for 4h;Reflux;	General procedure: A mixture of 2-aminophenol derivative (5 mmol) and triethyl orthoformate (15 mL) was heated at reflux for 4 h. After cooling to room temperature, remained triethyl orthoformate was removed under reduced pressure and the residue was purified by column chromatography on silica gel.

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 11511 - 11515
[2]Journal of the Chinese Chemical Society,2015,vol. 62,p. 412 - 419
[3]Tetrahedron,2013,vol. 69,p. 6627 - 6633
[4]Comptes Rendus Chimie,2013,vol. 16,p. 1029 - 1034
[5]Angewandte Chemie - International Edition,2009,vol. 48,p. 9127 - 9130
[6]Chemistry - A European Journal,2011,vol. 17,p. 8294 - 8298
[7]Tetrahedron Letters,2012,vol. 53,p. 4588 - 4590
[8]Green Chemistry,2013,vol. 15,p. 2365 - 2368
[9]Organic Preparations and Procedures International,2013,vol. 45,p. 57 - 65
[10]Organic Letters,2011,vol. 13,p. 522 - 525
[11]Journal of Molecular Catalysis A: Chemical,2010,vol. 328,p. 119 - 123
[12]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997
[13]Angewandte Chemie - International Edition,2013,vol. 52,p. 4457 - 4461
Angew. Chem.,2013,vol. 125,p. 4553 - 4557,5
[14]Journal of Organic Chemistry,2019,vol. 84,p. 6868 - 6878

17
[ 99-57-0 ]
[ 149-73-5 ]
[ 70886-33-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	for 12h;Reflux;	A solution of 2-amino-4-nitrophenol (600 mg, 3.9 mmol) in trimethyl orthoformate (30 ml)was stirred at reflux for 12 hours_ The reaction mixture was slowly poured into ice-coldwater (100 ml)and extractedwith ethyl acetate (100 ml). The organiclayer was concentrated under reduced pressureand the residue 10 was purified by silica gel column chromatography eluting with dichloromethane: methanol=301to afford 5-nitrobenzo[d]oxazole as a white solid (530 mg, 83%).LCMS (ESI):mlz = 164.0 [M+H(
75%	for 12h;Reflux;	A solution of 2-amino-4-nitrophenol (5.0 g, 32 mmol) in trimethoxymethane (60 mL) was stirred at reflux for 12 h. The reaction mixture was poured into ice water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The concentrate was purified by column chromatography (n-Hex/EtOAc=8/1) to afford 5-nitrobenzo[d]oxazole as an orange solid (4.0 g, 75%). LC/MS (ES+): m/z calculated for C7H4N2O3: 164.0; found: 165.1 [M+H]. 1H NMR (400 MHz, CDCl3): delta 8.71 (d, J=1.6 Hz, 1H), 8.39-8.36 (dd, J=9.0 Hz, 1.8 Hz, 1H), 8.27 (s, 1H), 7.73 (d, J=8.8 Hz, 1H).
75%	for 12h;Reflux;	Step 1: A solution of 2-amino-4-nitrophenol (5.0 g, 32 mmol) in trimethoxymethane (60 mL) was stirred at reflux for 12 h. The reaction mixture was poured into ice water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2S04, and concentrated under reduced pressure. The concentrate was purified by column chromatography (n-Hex/EtOAc = 8/1) to afford 5-nitrobenzo[d]oxazole as an orange solid (4.0 g, 75%). LC/MS (ES+): m/z calculated for C7H4N2O3: 164.0; found: 165.1 [M+H]. NMR (400 MHz, CDCb): d 8.71 (d, J- 1.6 Hz, 1H), 8.39-8.36 (dd, J = 9.0 Hz, 1.8 Hz, 1H), 8.27 (s, 1H), 7.73 (d, j= 8.8 Hz, 1H).

Reference： [1]Patent: WO2015/154023,2015,A1 .Location in patent: Page/Page column 228; 229
[2]Patent: WO2020/36574,2020,A1 .Location in patent: Page/Page column 69-70
[3]Patent: US2020/55871,2020,A1 .Location in patent: Paragraph 0489
[4]Journal of Molecular Catalysis A: Chemical,2010,vol. 328,p. 119 - 123

18
[ 70886-33-8 ]
[ 124-38-9 ]
[ 638-45-9 ]
[ 1260071-12-2 ]

Reference： [1]RSC Advances,2017,vol. 7,p. 52496 - 52502
[2]Angewandte Chemie - International Edition,2010,vol. 49,p. 8670 - 8673

19
[ 70886-33-8 ]
[ 121-44-8 ]
[ 78096-54-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 522 - 525

20
[ 230-27-3 ]
[ 70886-33-8 ]
[ 1264661-18-8 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 2160 - 2162

21
[ 70886-33-8 ]
[ 112-55-0 ]
[ 1321878-10-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5456 - 5462

22
[ 123-75-1 ]
[ 70886-33-8 ]
[ 1323158-73-1 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 8294 - 8298

23
[ 70886-33-8 ]
[ 98-09-9 ]
[ 891-43-0 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 11522 - 11524

24
[ 110-89-4 ]
[ 70886-33-8 ]
C₁₂H₁₅N₃O₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 11511 - 11515

25
[ 70886-33-8 ]
[ 3053-37-0 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 11511 - 11515

26
[ 70886-33-8 ]
[ 1246472-00-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A 500 mL 3-neck round bottom flask equipped with a septum, thermocouple, 125 mL addition funnel, inert gas inlet and magnetic stir bar was purged with nitrogen for 10 min. Hexamethyldisilazane (42 mL, 0.20 mol) and THF (78 mL) were charged against positive nitrogen pressure. The addition funnel was charged with a hexane solution of n-butyllithium (78.0 mL, 195 mmol). The amine solution was cooled to -52 C and n-butyllithium was added over 84 min, resulting in a temperature increase to 12.5 C over the course of the addition. The resulting lithium hexamethyldisilazide solution was removed from the cooling bath and aged for 30 min.To a 500 mL 3-neck round bottom flask equipped with a septum, thermocouple, inert gas inlet and magnetic stir bar was charged 5-chlorobenzoxazole (20.00 g, 130 mmol). The gray solid was dissolved in THF (100 mL) and the resulting colorless solution was cooled to -25 C. The freshly prepared lithium hexamethyldisilazide solution was added via cannula over 80 min. The temperature of the anion solution was maintained between -25 and -15 C during the addition. The resulting dark brown solution was aged for 90 min between -25 and -15 C.To a 1000 mL 3-neck round bottom flask equipped with a Claisen adapter, septum, thermocouple, inert gas inlet, stir shaft bearing, and blade was charged THF (100 mL) and N-bromosuccinimide (34.8 g, 195 mmol). The resulting slurry was cooled to -20 C and the anion solution was added via cannula over 150 min. During the addition the anion solution and reaction mixture were maintained between -25 and -15 C. The resulting brown slurry was removed from the cooling bath and aged for 50 min while warming to room temperature.To the resulting bromide slurry was added a solution of ethanolamine (12.6 mL, 208 mmol) in MeCN (38 mL) via syringe pump over 5 h. During the addition the reaction temperature was maintained between 20 and 27 C. The resulting brown slurry was aged at room temperature overnight.The reaction mixture was cooled in an ice water bath and the septum replaced with a 50 mL addition funnel charged with concentrated HCl (32 mL, 390 mmol). The acid solution was added over 10 min, during which time the temperature increased from 10 to 20 C. The reaction mixture was removed from the ice water bath and aged for 5 min. Charged 20 wt % aqueous K2HPO4 (170 mL) and the resulting biphasic mixture was transferred to a separatory funnel. The flask was washed with THF (3×, 10 mL) and the washings were added. The aqueous phase was cut. The organic phase was washed with 20 wt % aqueous K2HPO4 (200 mL), separated and analyzed. The crude reaction stream had a total mass of 396.47 g. By quantitative HPLC assayed 25.81 g of 2 in the organic phase, 93% assay yield, 92.74 LC peak area percent at 210 nm. Pure 2 was obtained on a small (1 g) scale by silica gel chromatography (3:1 to 1:3 hexanes/EtOAc eluent).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 730 - 732

27
[ 70886-33-8 ]
[ 1356342-18-1 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 730 - 732

28
[ 70886-33-8 ]
[ 824-79-3 ]
[ 112606-69-6 ]

Yield	Reaction Conditions	Operation in experiment
72%		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

29
[ 70886-33-8 ]
[ 25563-06-8 ]
[ 112606-69-6 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 4214 - 4216

30
[ 5436-01-1 ]
[ 70886-33-8 ]
[ 1366397-70-7 ]

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

31
[ 70886-33-8 ]
[ 49559-61-7 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3986 - 3989

32
[ 70886-33-8 ]
[ 124-38-9 ]
[ 49559-67-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3986 - 3989

33
[ 70886-33-8 ]
[ 3240-34-4 ]
[ 891-43-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 1,10-Phenanthroline; palladium diacetate; caesium carbonate; In dimethyl sulfoxide; at 150℃; for 36h;Inert atmosphere;	Gerenal procedure: Under N2, a reaction tube was charged with benzoxazole (0.2 mmol), PhI(OAc)2 (80.5 mg, 0.25 mmol), Pd(OAc)2 (2.2 mg, 5 mol %), 1,10-phenanthroline (7.9 mg, 10 mol %) and DMSO (2 mL). The mixture was stirred at 150 C for 20 h. After the completion of the reaction, as monitored by TLC, 10 mL of ethyl acetate was added and the mixture was washed with water (3 × 5 mL). Then the organic layer was concentrated in vacuo and the residue was purified by flash column chromatography on a silica gel to give the desired product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4588 - 4590

34
[ 70886-33-8 ]
[ 16308-16-0 ]
[ 112606-69-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	With 1,10-Phenanthroline; palladium diacetate; caesium carbonate; In dimethyl sulfoxide; at 150℃; for 20h;Inert atmosphere;	Gerenal procedure: Under N2, a reaction tube was charged with benzoxazole (0.2 mmol), PhI(OAc)2 (80.5 mg, 0.25 mmol), Pd(OAc)2 (2.2 mg, 5 mol %), 1,10-phenanthroline (7.9 mg, 10 mol %) and DMSO (2 mL). The mixture was stirred at 150 C for 20 h. After the completion of the reaction, as monitored by TLC, 10 mL of ethyl acetate was added and the mixture was washed with water (3 × 5 mL). Then the organic layer was concentrated in vacuo and the residue was purified by flash column chromatography on a silica gel to give the desired product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4588 - 4590

35
[ 70886-33-8 ]
[ 221044-05-9 ]
[ 1402228-03-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; silver carbonate; Trimethylacetic acid; In 1,2-dichloro-benzene; at 140℃; for 24h;Schlenk technique; Sealed tube;	General procedure: A 25 mL flame-dried Schlenk tube was charged with the1-(pyrimid-2-yl)-1H-indoles 1 (0.25 mmol), 1,3-azoles2 (0.75 mmol), [RhCp*Cl2]2 (3.9 mg, 2.5 mol%), AgSbF6(8.6 mg, 10 mol%), pivalic acid (PivOH,51 mg, 0.50 mmol), Ag2CO3 (6.9 mg, 10 mol%), and DCB(1.0 mL). The tube was sealed under an O2 atmosphere.The reaction mixture was stirred vigorously and heated at140 C for 24 h, and then cooled to ambient temperature.The final reaction mixture was diluted with 10-20 mL ofCH2Cl2, filtered through a Celite pad to remove insolublesalts, and then washed with 10-20 mL of CH2Cl2. Thecombined CH2Cl2 extracts were concentrated in a vacuumevaporator and the crude product was purified by flashcolumn chromatography on silica gel (petroleum ether/ethylacetate=3/1, v/v) to give the desired product 3 or 4.

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997
[2]Science China Chemistry,2018,vol. 61,p. 200 - 205

36
[ 70886-33-8 ]
[ 71-43-2 ]
[ 891-43-0 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 8964 - 8966

37
[ 70886-33-8 ]
[ 13360-57-1 ]
N,N-dimethyl-5-nitro-1,3-benzoxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium dichromate; dichloro(2,2'-bipyridine)palladium(II); copper(l) cyanide; potassium carbonate; In chlorobenzene; at 150℃; for 24h;Sealed tube; Molecular sieve;	General procedure: Under air, a reaction tube was charged with benzoxazole (0.2 mmol), dimethylsulfamoyl chloride (0.3 mmol), BipyPdCl2 (10 mol %), CuCN (20 mol %), K2CO3 (0.4 mmol), K2Cr2O7 (0.2 mmol) and dry PhCl (2 mL). The mixture was stirred at 150 o C for 24 h. After the completion of the reaction, monitored by TLC, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6297 - 6299,3

38
[ 70886-33-8 ]
[ 299199-50-1 ]
3-(5-nitrobenzoxazol-2-yl)-N-(quinolin-8-yl)thiophene-2-carboxamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 4457 - 4461
Angew. Chem.,2013,vol. 125,p. 4553 - 4557,5

39
[ 70886-33-8 ]
[ 5542-49-4 ]
[ 3053-37-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	With triphenylphosphine; copper(l) chloride; lithium tert-butoxide; In tetrahydrofuran; at 20℃; for 1h;	General procedure: A 20 mL oven-dried and N2-flushed scintillation vial equipped with a magnetic stir bar was charged with a mixture of azole 1 or 4 (1.00 mmol, 1.00 equiv), CuCl (4.50 mg, 0.05 mmol, 0.05 equiv), PPh3 (26.3 mg, 0.10 mmol, 0.10equiv), LiOtBu (0.24 g, 3.00 mmol, 3.00 equiv), and O-benzoyl hydroxyl amine 3 (1.50 mmol, 1.50 equiv), and tetrahydrofuran (THF) (4.00 mL, 0.25 M concentration of substrate). The vial was capped and the mixture was stirred at room temperature for 1 h. After the reaction was complete, distilled deionized H2O (10 mL) was added, and the mixture was extracted with EtOAc (2 × 15 mL). The solution was concentrated in vacuo, and the crude product was purified by SiO2 column chromatography to afford adesired benzoxazole derivative.

Reference： [1]Tetrahedron,2013,vol. 69,p. 6627 - 6633

40
[ 70886-33-8 ]
[ 104-87-0 ]
[ 112606-69-6 ]

Reference： [1]RSC Advances,2018,vol. 8,p. 11127 - 11133
[2]Green Chemistry,2013,vol. 15,p. 2365 - 2368

41
[ 85-44-9 ]
[ 70886-33-8 ]
[ 1400811-41-7 ]

Reference： [1]Indian Journal of Heterocyclic Chemistry,2012,vol. 21,p. 381 - 382

42
[ 108-31-6 ]
[ 70886-33-8 ]
[ 1400811-44-0 ]

Reference： [1]Indian Journal of Heterocyclic Chemistry,2012,vol. 21,p. 381 - 382

43
[ 108-30-5 ]
[ 70886-33-8 ]
[ 1400811-47-3 ]

Reference： [1]Indian Journal of Heterocyclic Chemistry,2012,vol. 21,p. 381 - 382

44
[ 2058-74-4 ]
[ 70886-33-8 ]
3-hydroxy-1-methyl-3-(5-nitrobenzo[d]oxazol-2-yl)indolin-2-one [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5270 - 5273

45
[ 70886-33-8 ]
[ 611-73-4 ]
[ 7653-47-6 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 16705 - 16709

46
[ 23328-69-0 ]
[ 70886-33-8 ]
[ 78096-53-4 ]

Reference： [1]Synlett,2014,vol. 25,p. 2013 - 2018

47
[ 110-91-8 ]
[ 70886-33-8 ]
[ 78096-53-4 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 12784 - 12789
[2]Journal of Organic Chemistry,2014,vol. 79,p. 9613 - 9618
[3]Molecular catalysis,2018,vol. 450,p. 104 - 111
[4]Catalysis science and technology,2020,vol. 10,p. 940 - 943

48
[ 70886-33-8 ]
[ 98-80-6 ]
[ 891-43-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With iron(III) oxide; copper(l) iodide; 1,10-Phenanthroline; di-tert-butyl peroxide; lithium tert-butoxide; In toluene; at 110℃; for 12h;Schlenk technique; Sealed tube; Green chemistry;	General procedure: CuI (0.1 mmol), Fe2O3(0.1 mmol), 1,10-phenanthroline(0.1mmol) ,LiOBu-t(1.0 mmol), t-BuOOBu-t(1.0 mmol), benzooxazole(0.5 mmol) and phenylboronic acid(1.0 mmol)were weighed into an oven-dried Schlenk tube which was sealed with a plug. Then toluene(3.0 mL) was added.The reaction mixture was stirred at 110 oC for 12 h. The resulting mixture was then cooled to room temperatureand diluted with ethyl acetate. The organic layer was collected, washed with water and brine, and dried overNa2SO4. After removal of the solvent in vacuo, the residue was purified by silica gel chromatography to give thedesired 2-phenyl<strong>[70886-33-8]benzo[d]oxazole</strong>.

Reference： [1]Synthesis,2015,vol. 47,p. 42 - 48

49
[ 70886-33-8 ]
[ 637-44-5 ]
5-nitro-2-(phenylethynyl)benzoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); silver(l) oxide; In N,N-dimethyl-formamide; at 80℃;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), silver(I) oxide (229 mg, 1 mmol) and aryl propiolic acid (1 mmol), under air, were added. Azole substrate (0.5 mmol) in DMF (4 mL) was added to the reaction mixture. The reaction mixture was stirred at 80 C for 6-8 h. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice cold water and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981

50
[ 70886-33-8 ]
[ 4843-42-9 ]
2-(naphthalen-1-ylethynyl)-5-nitrobenzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); silver(l) oxide; In N,N-dimethyl-formamide; at 80℃;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), silver(I) oxide (229 mg, 1 mmol) and aryl propiolic acid (1 mmol), under air, were added. Azole substrate (0.5 mmol) in DMF (4 mL) was added to the reaction mixture. The reaction mixture was stirred at 80 C for 6-8 h. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice cold water and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981

51
[ 70886-33-8 ]
[ 160542-02-9 ]
5-nitro-2-((4-(trifluoromethoxy) phenyl)ethynyl)benzoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); caesium carbonate; silver(l) oxide; In N,N-dimethyl-formamide; at 85℃; for 8h;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol percent), cesium carbonate (325 mg, 1 mmol), silver(I) oxide (229 mg, 1 mmol) and azole substrate (0.5 mmol) in 2 mL DMF, under air, were added. Phenyl acetylene substrate (1 mmol) in DMF (2 mL) was added to the reaction vessel slowly by dropping funnel over 2 h while stirring the reaction mixture on preheated oil bath at 85 °C. The reaction was allowed to stir for 6 h at the same temperature. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice coldwater and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981

52
[ 70886-33-8 ]
[ 536-74-3 ]
5-nitro-2-(phenylethynyl)benzoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); caesium carbonate; silver(l) oxide; In N,N-dimethyl-formamide; at 85℃; for 8h;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), cesium carbonate (325 mg, 1 mmol), silver(I) oxide (229 mg, 1 mmol) and azole substrate (0.5 mmol) in 2 mL DMF, under air, were added. Phenyl acetylene substrate (1 mmol) in DMF (2 mL) was added to the reaction vessel slowly by dropping funnel over 2 h while stirring the reaction mixture on preheated oil bath at 85 C. The reaction was allowed to stir for 6 h at the same temperature. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice coldwater and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981

53
[ 70886-33-8 ]
(R)-N-(1-(1-(benzo[d]oxazol-5-yl)-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl)-3-methyl-1-oxobutan-2-yl)-2-fluoro-5-(trifluoromethyl)benzamide [ No CAS ]