1105039-88-0 | 1-(4-Methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$14.00	$10.00
1g	97%	in stock	$55.00	$39.00
5g	97%	in stock	$274.00	$192.00

Description

• Catalog Number: AE31814
• Chemical Name: 1-(4-Methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole
• CAS Number: 1105039-88-0
• Molecular Formula: C17H23BN2O3
• Molecular Weight: 314.1871
• MDL Number: MFCD16877287
• SMILES: COc1ccc(cc1)Cn1ncc(c1)B1OC(C(O1)(C)C)(C)C

Computed Properties

• Complexity: 395
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 23
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4

Upstream Synthesis Route

The synthesis route for 1-(4-Methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole can be outlined as follows:

1. Synthesis of 4-Methoxybenzyl alcohol (Anisic alcohol):
Starting with 4-methoxybenzaldehyde (p-Anisaldehyde), perform a catalytic hydrogenation using a suitable catalyst (e.g., palladium on carbon, Pd/C) under hydrogen atmosphere to reduce the aldehyde group to the corresponding alcohol, yielding 4-methoxybenzyl alcohol.

2. Preparation of 4-Methoxybenzyl bromide:
Convert the 4-methoxybenzyl alcohol to 4-methoxybenzyl bromide through a bromination reaction using hydrobromic acid (HBr) or bromine (Br2) in the presence of a strong acid like sulfuric acid (H2SO4) or phosphoric acid (H3PO4) to facilitate the substitution.

3. Synthesis of 1H-pyrazole:
Start with the appropriate diketone and hydrazine (or a suitable hydrazine derivative) and carry out a condensation reaction to form the pyrazole ring. Ensure rigorous control of reaction conditions to favor the formation of the 1H-pyrazole isomer.

4. Borylation to introduce the boronate ester:
Using bis(pinacolato)diboron ([B2(pin)2]), conduct a Miyaura borylation reaction on the 1H-pyrazole derivative in the presence of a palladium catalyst (e.g., Pd(PPh3)4) and a base (e.g., KOAc) to introduce the 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group at the 4-position of the pyrazole ring.

5. Final benzylation to obtain the target compound:
React the 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole with 4-methoxybenzyl bromide in the presence of a base (e.g., NaH or K2CO3) to perform a nucleophilic substitution, introducing the 4-methoxybenzyl group at the N1 position of the pyrazole ring. This reaction can be performed in a suitable solvent like dimethylformamide (DMF) or acetonitrile (MeCN).

Each step should be closely monitored with appropriate analytical techniques such as NMR, GC-MS, or HPLC to ensure purity and confirm the structure of intermediates and the final product. It is important to carefully consider the choice of solvents, catalysts, and reaction conditions at each step to optimize the yield and selectivity of the desired compound.