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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2-Methylbenzoxazole is an endogenous metabolite.
Synonyms: 2-Methylbenzoxazole
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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 95-21-6 |
Formula : | C8H7NO |
M.W : | 133.15 |
SMILES Code : | CC1=NC2=CC=CC=C2O1 |
Synonyms : |
2-Methylbenzoxazole
|
MDL No. : | MFCD00005771 |
InChI Key : | DQSHFKPKFISSNM-UHFFFAOYSA-N |
Pubchem ID : | 7225 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H227-H315-H319 |
Precautionary Statements: | P210-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | a 2-Bromomethylbenzoxazole Following the procedure of Example 4(a), except using 2-methylbenzoxazole in place of 2-methylbenzothiazole, the title compound (2.22 g, 70%) was prepared as a yellow oil: 1 H NMR (250 MHz, DMSO-d6) delta 5.17 (s, 2H), 7.55 (m, 2H), 8.01 (d, J=7.9, 1.8 Hz, 1H), 8.20 (dd, J=7.9, 1.8 Hz, 1H). | |
45% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 12.0h;Reflux; | Under stirring, to a solution of 2-methylbenzoxazole (665 mg, 5 mmol) in carbon tetrachloride (16 mL), Add N-bromosuccinimide (890 mg, 5 mmol) Azoisobutyronitrile (188 mg, 1.15 mmol) and the mixture was stirred at reflux for 12 h. Cooled, filtered, and the filtrate was concentrated and the residue was chromatographed to give the title compound as a pale yellow oil (471 mg, yield 45%). |
17% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux; | A solution of 35 g (0.263 mol) of 2-methyl-benzooxazole in CC14 (300 mL) was treated with 47 g (0.263, 1 eq) of NBS and 1 g of benzoyl peroxide. The mixture was refluxed (100C) over night then cooled. Succinimide was filtered off and the mixture was evaporated to dryness. Column chromatography yielded 9.2 g (17%) of 2-bromomethyl- benzooxazole as a light yellow oil, MS: 210,212 (MH+). (H. Uno, M. Kurokawa, Y. Masuda, Chem. Pharm. Bull., 1981,29, 2359). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 1-(N-ferrocenylmethyl)benzimidazole grafted onto Merrifield resin; In dimethyl sulfoxide; at 140℃; for 24h; | General procedure: A mixture of N-(2-iodoaryl)benzamides/acetamide/propanamide (1 mmol) and [FemMerBenz]OH (100 mg, 0.12 mmol) in dry DMSO (5 mL) was stirred for 15-24 h at 140 C. The reaction mixture was filtered and quenched withwater (10 mL). The resultant solutionwas extracted with ethyl acetate (3*10 mL). The combined organic layers were dried over Na2SO4. The solventwas evaporated in vacuo to give the crude product, which was purified by column chromatography over silica gel using hexane/EtOAc as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With tetra-(n-butyl)ammonium iodide; 1,2-dichloro-ethane; urea; at 110℃; for 2h;Microwave irradiation; | General procedure: 2-Methylquinolines 1(2 mmol), TBAI (2 mmol), urea (2 mmol), and 1,2-dichloroethane (10 mL) weremixed in a microwave tube. The reaction mixture was stirred at 110 C for 30 min under microwave irradiation using a CEM Discover microwave reactor(the highest power: 150 W; run time: 5 min; hold time: 30 min; temperature:110 C). The resulting reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel using hexane/EtOAc as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With piperidine; In neat (no solvent); at 160℃; for 4h;Microwave irradiation; | General procedure: A reaction vessel was charged with 1H-indole-3-carbaldehyde 1a-d (2.5 mmol),2-methylhetarene 2a-c (3.0 mmol), and piperidine (0.05 ml, 0.5 mmol), and the mixture was stirred and heated in microwave reactor at 160 C for 4 h. Then, the reaction mixture was cooled down and quantitatively transferred to another vessel employing CH2Cl2 (3×10 ml). Solutions of compounds 3aa and 3ac were evaporated in vacuum and the residual solids were recrystallized from EtOH. Solutions of other products were concentrated and the residues were purified by flash column chromatography on silica gel eluting with 5% solution of isopropanol in CH2Cl2. Note: DBU (0.075 ml, 0.5 mmol) was used as a base to perform reaction between 1H-indole-3-carbaldehyde(1a) and 2-methylpyridine (2b); the mixture wasmicrowaved at 240 for 2 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In acetic anhydride; at 150℃; for 18h; | A mixture of 0.4 g (3 mmol) of 2-methylbenzo[d]oxazole, 2.92 g (12 mmol) of 5-nitro-2-furaldehyde diethyl ester and 100 ml of acetic anhydride was heated at 150 C for 18 hours (monitored by thin layer chromatography). After the mixture was cooled, concentration in vacuo to remove solvent afforded a crude product, chromatography (FC, silica gel, methanol: dichloromethane = 1: 15) purification,(E)-2-[2-(5-nitrofuran-2-yl)ethenyl]benzo[d]oxazole (Compound 3, 0.33 g, 43% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Under nitrogen protection conditions,2.2 g (19.6 mmol) of potassium tert-butoxide was added to 20 mL of anhydrous tetrahydrofuran,Then stirred under ice-cooling for 10 minutes,The suspension was added dropwise1.3 mL (10.8 mmol) of 2-methylbenzoxazole,Under this condition, stirring was continued for 10 min,A solution containing N- (4-formylphenyl) carbazole (9.8 mmol) in dry tetrahydrofuran was slowly added to the above solution,After stirring for 2 hours,The mixture was poured into 200 mL of water,Extracted three times with dichloromethane (50 mL x 3)Combined organic layer,Washed with water, dried Na2SO4,Vacuum distillation, remove the organic solvent,The residue was purified by silica gel column chromatography,The eluent is dichloromethane,And recrystallized from n-Hexane-CH2Cl2 to give pure pale yellow product. Yield: 45%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 72h; | 3.84 g (14.15 mmol) of N-phenyl-3-formyl carbazole was added to a 100 mL single-mouth flask.2.26 g (16.98 mmol) of 2-methylbenzoxazole, 2.50 g (44.64 mmol) of KOH, and then about 60 mL of DMF.After stirring for 3 d at room temperature, the reaction was monitored by TLC (EA/PE = 1:3).The reaction solution was poured into a large amount of cold water, and DMF was washed away, and a large amount of brown precipitate was precipitated, and suction-filtered to obtain a brown crude product [Note: The filtration process was extremely slow].Using EA/PE=1:50 as eluent and 200~300 mesh silica gel to obtain a relatively pure crude yellow solid.Further, it was recrystallized three times with a DCM/PE mixture to obtain 2.24 g of a yellow solid powder, yield 41%. |