885518-82-1 | 3-Iodo-1H-indazole-6-carboxylic acid methyl ester

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$7.00	$5.00
1g	95%	in stock	$12.00	$9.00
10g	95%	in stock	$95.00	$67.00

Description

• Catalog Number: AD88348
• Chemical Name: 3-Iodo-1H-indazole-6-carboxylic acid methyl ester
• CAS Number: 885518-82-1
• Molecular Formula: C9H7IN2O2
• Molecular Weight: 302.0686
• MDL Number: MFCD07781616
• SMILES: COC(=O)c1ccc2c(c1)[nH]nc2I

Computed Properties

• Complexity: 237
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 2.1

Upstream Synthesis Route

The upstream synthesis route for 3-Iodo-1H-indazole-6-carboxylic acid methyl ester could proceed as follows:

1. **Synthesis of Methyl 6-Iodoindazole-1-carboxylate:**
- Start with commercially available 6-iodoindazole as the substrate.
- Esterify the carboxylic acid group by reacting it with methanol in the presence of a catalytic amount of sulfuric acid or other suitable esterification catalysts like HCl or DCC / DMAP to yield methyl 6-iodoindazole-1-carboxylate.

2. **N-Substitution to form the 1H-indazole ring:**
- Perform a nucleophilic substitution by treating the methyl 6-iodoindazole-1-carboxylate with hydrazine hydrate in the presence of a base such as potassium hydroxide.
- This will yield 6-iodo-1H-indazole-1-carboxylic acid methyl ester.

3. **Introduction of the 3-iodo substituent:**
- The preceding step could afford a mixture of regioisomers, possibly including some amount of the desired 3-iodo-1H-indazole-6-carboxylic acid methyl ester, but to specifically introduce the 3-iodo substituent at a later stage, an alternative would be to start with an appropriate indazole derivative that allows for ortho halogenation.
- Halogenation at the desired position can be achieved via an electrophilic aromatic substitution using iodine in the presence of oxidizing agents like oxone, or by using I2 with silver(I) oxide as the oxidant in a suitable solvent like acetonitrile or dichloromethane under controlled temperature conditions.

4. **Optimization and Purification:**
- Optimize yields and reaction conditions at each step by monitoring the reactions using thin-layer chromatography (TLC) or high-performance liquid chromatography (HPLC).
- Purify the final product, 3-Iodo-1H-indazole-6-carboxylic acid methyl ester, via column chromatography or recrystallization techniques, and confirm the structure using nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS).

This synthetic route involves multi-step organic synthesis skills, including esterification, nucleophilic substitution, and electrophilic halogenation. Each step should be validated for yield and purity, with careful attention to regio-selectivity, especially during halogenation steps.