1-(Tetrahydropyran-4-yl)-1H-pyrazole-4-boronic acid pinacol ester
1-(Tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
CAS: 1040377-03-4
Molecular Formula: C14H23BN2O3
1-(Tetrahydropyran-4-yl)-1H-pyrazole-4-boronic acid pinacol ester - Names and Identifiers
1-(Tetrahydropyran-4-yl)-1H-pyrazole-4-boronic acid pinacol ester - Physico-chemical Properties
| Molecular Formula | C14H23BN2O3 |
| Molar Mass | 278.15 |
| Density | 1.16 |
| Melting Point | 113.0 to 117.0 °C |
| Boling Point | 413.8±35.0 °C(Predicted) |
| Appearance | White solid |
| Color | White to Light yellow |
| pKa | 2.70±0.19(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Sensitive | Irritant |
| MDL | MFCD12033229 |
1-(Tetrahydropyran-4-yl)-1H-pyrazole-4-boronic acid pinacol ester - Reference Information
| Use | 1-(tetrahydropyran-4-yl)-1H-pyrazol-4-borate pinacol ester is a 1-Substituted-1H-pyrazol-4-borate pinacol ester. 1-substituted-1H-pyrazol-4-borate pinacol ester is a kind of relatively novel compounds and important pharmaceutical intermediates, which has a wide range of application prospects, such as crizotinib intermediate 1-(1-tert-butoxycarbonylpiperidine-4-yl) pyrazol-4-borate pinacol ester. |
| preparation | step 1: synthesis of compound tetrahydro-2H-pyran-4-methylsulfonate add TEA(9mL,63.9mmol) to methylene chloride (60mL) solution of tetrahydropyran-4-ol (4mL,41.11mmol) at 0 ℃, stir for 5min and slowly add methyl sulfonyl chloride (3.5mL,45mmol), after continuing the reaction for 1h, the room temperature reaction was restored overnight. Water (50mL) was added to the reaction solution, methylene chloride (100mL × 3) was extracted, and the organic phase was dried with anhydrous Na2SO4 and concentrated to obtain 7g yellow solid with a yield of 94.5%. MS(ESI,pos.ion)m/z: no response. Step 2: Synthesis of Compound 1-(Tetrahydropyran -4-yl)-1H-pyrazole -4-borate pinacol ester; Tetrahydro-2H-pyran -4-methylsulfonate ester (2.8g,16mmol), 4-pyrazole borate pinacol ester (2.01g,10.4mmol) and cesium carbonate (5.4g,17mmol) were mixed and DMF(30mL) was added to react overnight at 100 ℃. The reaction solution was concentrated under reduced pressure to remove DMF, water (20mL) was added, methylene chloride (30mL × 3) was extracted, the organic phase was dried with anhydrous Na2SO4, and the concentrated crude product was prepared, separated and purified by HPLC to obtain 1.1g yellow oil with a yield of 38%. MS(ESI,pos.ion)m/z:279.3[M 1]. |
Last Update：2024-04-10 22:30:50
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