Pyrazole-4-boronic acid pinacol ester

• CAS: 269410-08-4
• Catalog Number: ACM269410084-2
• Category: Other
• Molecular Weight: 194.04g/mol
• Molecular Formula: C9H15BN2O2
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CNN=C2
• InChI: InChI=1S/C9H15BN2O2/c1-8(2)9(3,4)14-10(13-8)7-5-11-12-6-7/h5-6H,1-4H3,(H,11,12)
• InChI Key: TVOJIBGZFYMWDT-UHFFFAOYSA-N
• Complexity: 217
• Covalently-Bonded Unit Count: 1
• Exact Mass: 194.122658g/mol
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Heavy Atom Count: 14
• Monoisotopic Mass: 194.122658g/mol
• Rotatable Bond Count: 1

Case Study

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for the Synthesis of Drug-Like Pyrazoles

Mosallanejad, Arash, et al. Tetrahedron Letters, 2018, 59(18), 1708-1710.

A solution of (cyanomethylene)tributylphosphorane (262 L, 1.00 mmol), (tetrahydrofuran-3-yl)methanol (51 mg, 0.50 mmol), and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (97 mg, 0.5 mmol) in degassed 1,4-dioxane (2 mL) was prepared in a sealed microwave tube at room temperature under nitrogen. The solution was subjected to microwave irradiation at 150 °C for 30 minutes and then allowed to cool to room temperature.
· Subsequently, 1-bromo-4-methoxybenzene (94 mg, 0.50 mmol), potassium carbonate (207 mg, 1.50 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (40.8 mg, 0.05 mmol) were introduced to the solution under vacuum and nitrogen. After adding degassed water (1 mL) under nitrogen, the mixture was stirred at 120 °C for 20 minutes.
· The reaction mixture was then diluted with EtOAc (25 mL) and water (15 mL), followed by extraction of the aqueous layer with EtOAc (15 mL). The combined organic layers were washed with saturated brine (15 mL), dried with MgSO4, filtered, and concentrated to yield the crude product.
· The crude product was further purified by preparative HPLC (5µ silica, 30 mm diameter, 100 mm length), using a gradient of water (with 1% NH3OH) and MeCN as eluents to obtain 4-(4-methoxyphenyl)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrazole (89 mg, 69%) in the form of a beige solid.

Custom Q&A

What is the IUPAC Name of the compound?

The IUPAC Name of the compound is 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

What is the molecular formula of the compound?

The molecular formula is C9H15BN2O2.

What is the CAS number of the compound?

The CAS number of the compound is 269410-08-4.

What is the molecular weight of the compound?

The molecular weight of the compound is 194.04 g/mol.

How many hydrogen bond donor counts does the compound have?

The compound has 1 hydrogen bond donor count.

How many hydrogen bond acceptor counts does the compound have?

The compound has 3 hydrogen bond acceptor counts.

How many rotatable bond counts does the compound have?

The compound has 1 rotatable bond count.

What is the exact mass of the compound?

The exact mass of the compound is 194.1226579 g/mol.

What is the topological polar surface area of the compound?

The topological polar surface area of the compound is 47.1Ų.

Is the compound canonicalized?

Yes, the compound is canonicalized.

Synthetic Use

Downstream Synthesis Route 1

• 269410-08-4

• 4843-98-5

Reference: [1] Patent: WO2008/116620, 2008, A1, . Location in patent: Page/Page column 171

Downstream Synthesis Route 2

• 269410-08-4
• 74-88-4

• 761446-44-0

Reference: [1] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 189

Downstream Synthesis Route 3

• 269410-08-4
• 74-83-9

• 761446-44-0

Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 24, p. 7934 - 7937

Downstream Synthesis Route 4

• 269410-08-4
• 96-32-2

• 959585-44-5

Reference: [1]Patent: WO2007/138472,2007,A2 .Location in patent: Page/Page column 32

Downstream Synthesis Route 5

• 269410-08-4
• 5292-43-3

• 1006875-83-7

Reference: [1]Patent: WO2016/123796,2016,A1 .Location in patent: Page/Page column 49; 50

Downstream Synthesis Route 6

• 269410-08-4
• 49844-90-8

• 77168-38-8

Reference: [1]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 41

* For details of the synthesis route, please refer to the original source to ensure accuracy.