1201186-54-0 | N-Tosyl-5-bromo-4,7-diazaindole

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$7.00	$5.00
250mg	98%	in stock	$10.00	$7.00
1g	98%	in stock	$37.00	$26.00

Description

• Catalog Number: AA33932
• Chemical Name: N-Tosyl-5-bromo-4,7-diazaindole
• CAS Number: 1201186-54-0
• Molecular Formula: C13H10BrN3O2S
• Molecular Weight: 352.2064
• MDL Number: MFCD12964053
• SMILES: Cc1ccc(cc1)S(=O)(=O)n1ccc2c1ncc(n2)Br

Computed Properties

• Complexity: 445
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 20
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• XLogP3: 2.9

Upstream Synthesis Route

The upstream synthesis route of N-Tosyl-5-bromo-4,7-diazaindole involves the following steps:

1. Diazotization: Starting from 4,7-diaminoindole, the first step is to selectively protect one amino group, followed by the diazotization of the other. This is typically achieved using reagents like t-butyl nitrite (TBN) in acidic conditions.

2. Bromination: The diazotized intermediate is then reacted with bromine (Br2) to introduce the bromo group at the 5-position of the indole ring. Careful control of the reaction conditions is necessary to ensure regioselectivity.

3. Protection of the amine: The remaining free amino group of the indole is then protected by tosylation using p-toluenesulfonyl chloride in the presence of a base such as triethylamine, to yield the N-Tosyl-5-bromoindole.

4. Diazaindole formation: Finally, the N-Tosyl group serves as a good leaving group for the closure of the diazaindole ring system upon appropriate reaction conditions, which could involve reagents like a carbonate base to facilitate the intramolecular attack of the nitrogen onto the tosyl-activated position.

Isolation and purification of N-Tosyl-5-bromo-4,7-diazaindole would involve standard techniques such as crystallization or chromatography. Each step may also require optimization to ensure high yield and purity of the desired product.