Structure of 1086391-06-1
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CAS No. : | 1086391-06-1 |
Formula : | C9H7BrN2O2 |
M.W : | 255.07 |
SMILES Code : | O=C(C1=CC2=C(NN=C2Br)C=C1)OC |
MDL No. : | MFCD11045401 |
InChI Key : | JEPZKKWEBQAHAO-UHFFFAOYSA-N |
Pubchem ID : | 45790261 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100℃; for 24h;Inert atmosphere; | Step 5. Methyl 3-pyridin-4-yl-lH-indazole-5-carboxylate 4-(4;4?5,5-Tetramethyl-l53,2-dioxaborolan-2-yl)pyridine (0.965 g, 4.70 mmol), PdCl2(dppf)-CH2Cl (0.256 g, 0.314 mmol), sodium carbonate (3.14 mL, 6.27 mmol) and methyl 3-bromo-lH-indazole-5-carboxylate (0.8 g, 3.14 mmol) were taken up in 1,4-dioxane (15 mL). The flask was evacuated and back-filled with N2 (x3) before stirring at 100 C for 24 hours. Room temperature was attained, the reaction mixture was diltuted with MeOH, filtered through Celite and concentrated in vacuo.Purification of the residue by MPLC (12-100% EtOAc-hexanes) gave methyl 3- pyridin-4-yl-lH-indazole-5-carboxylate as a yellow solid.MS (APCI) calculated for Ci4Hi2N302 [M+H]+, 254; found 254 (0.92 mins). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; | A mixture of compound 1 (1.7 g, 0.01 mol) and NBS (2.1 g, 0.012 mol) in THF (10 ml) was stirred at r.t. overnight. The mixture was concentrated to yield a residue, to which was added DCM (5 ml). After stirring for 30 min, the solution was filtered to yield compound 2 (1.9 g, 80%) as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With caesium carbonate; In dimethyl sulfoxide; at 20℃; | A mixture of compound 2 (1.0 g, 0.004 mol), 4-(2-chloroethyl)morpholine (1.2 g, 0.008 mol) and Cs2CO3 (2.5 g, 0.016 mol) in DMSO (10 ml) was stirred at r.t. overnight. Water (20 ml) was added to the reaction mixture, and then extracted with EA (50 ml×2). The organic layers were combined, dried and concentrated to a residue, which was re-crystallized by PE (10 ml) to afford compound 3 (500 mg, 70%) as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.04% | With copper diacetate; triethylamine; In dichloromethane; at 20℃; for 16h;Inert atmosphere; | Methyl 3-bromo-1H-indazole-5-carboxylate (5.00 g; 19.6 mmol; 1.00 eq.), dichloromethane (80.00 mL), triethylamine (5.43 mL; 39.2 mmol; 2.00 eq.), copper acetate (5.34 g; 29.4 mmol; 1.50 eq.) and 4-(tert-butoxycarbonyl)phenylboronic acid (8.97 g; 39.2 mmol; 2.00 eq.) were stirred in a round bottom flask for 16 h at room temperature. 200 mL of a mixture of NH4OH / NH4Cl sat. (1/1) and 50 mL of dichloromethane were added. The aqueous layer was extracted with another 50 mL of dichloromethane. The combined organic phases were washed three times with 50 mL of a saturated solution of NH4OH, and once with 50mL of water, dried over MgSO4and concentrated under vacuum. The residue was purified on silica gel chromatography using heptane/ethyl acetate (1/9) as eluent. Methyl 3-bromo-1-(4-tert-butoxycarbonylphenyl)indazole-5-carboxylate was isolated as a white powder (680 mg; 8.04percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In dichloromethane; at 20℃; | Into a 100-mL round-bottom flask, were placed a solution of methyl 3- bromo-1 H-indazole-5-carboxylate (3.0 g, 11.76 mmol) in dichloromethane (50 mL), 3,4-dihydro-2H-pyran (1.98 g, 23.54 mmol) and p-TsGH H20 (245 mg, 1.18 mmol). The resulting solution was stirred overnight at room temperature, and then concentrated under vacuum. The residue was recrystallized from DCM-Hexane (1 : 20) to yield methyl 3-bromo-1-(oxan-2-yl)-1 H-indazoie-5- carboxyiate as a yellow solid. LC/MS (ES, m/z): 339 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 20℃; for 4h;Inert atmosphere; | Into a 250-mL oven-dried round-bottom flask, were placed a solution of methyl 3-bromo-1 H-indazoie-5-carboxylate (5,0 g, 19,60 mmol) in CH3CN (150 mL), (chiorodiphenyimethyl)benzene (21 .9 g, 78.56 mmol) and potassium carbonate (13.8 g, 98.40 mmol). The resulting mixture was stirred under nitrogen for 4 h at room temperature, and the precipitate formed was collected by filtration. The residue was suspended in DCM (200 mL), and filtered to remove the insoluble material. The filtrate was concentrated under vacuum to yield methyl 3-bromo-1-(triphenylmethyi)-1 H-indazole-5-carboxyiate as a white solid. |
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