3-Chloro-5H-pyrrolo[2,3-b]pyrazine

Name: 3-Chloro-5H-pyrrolo[2,3-b]pyrazine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1111638-10-8
Cat. No. CS-W005881
Purity≥98%
MDL No.MFCD12024539

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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3-Chloro-5H-pyrrolo[2,3-b]pyrazine|CS-W005881

Structure of 1111638-10-8

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General Information

CAS No. 1111638-10-8
Cat. No. CS-W005881
Purity ≥98%
MDL No. MFCD12024539
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄ClN₃
Molecular Weight 153.57
Synonym(s) None
SMILES ClC1=NC2=C(C=CN2)N=C1

Description

3-Chloro-5H-pyrrolo[2,3-b]pyrazine is a heterocyclic scaffold featuring a chlorinated pyrrolopyrazine core, offering enhanced electron-deficient character and structural rigidity. This moiety integrates readily into pharmaceutical intermediates, enabling efficient coupling reactions under mild conditions. Its bench-stable nature and compatibility with diverse functional groups streamline synthetic workflows in medicinal chemistry.

Application

3-Chloro-5H-pyrrolo[2,3-b]pyrazine serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The chlorine atom at the 3-position exhibits high reactivity in Suzuki, Negishi, and Buchwald–Hartwig transformations, facilitating the construction of complex biaryl and amino-substituted scaffolds. Its planar, electron-deficient core enhances binding affinity in kinase inhibitors and other target-directed compounds. Bench-stable and readily purified by column chromatography, it functions reliably in multi-step syntheses for API development.

Synthesis

Route1
- 1111638-09-5
- ~62%
- In-stock
  
  1111638-10-8
References
- de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael Patent: US2011/59118 A1, 2011 ; Location in patent: Page/Page column 88-89 ;
Route2
- 1111638-09-5
- In-stock
  
  865-47-4
- 75-65-0
- ~61%
- In-stock
  
  1111638-10-8
References
- PFIZER INC. Patent: WO2009/16460 A2, 2009 ; Location in patent: Page/Page column 80 ; WO 2009/016460 A2

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 41.57
LogP 1.6113
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazine compounds

Key Words

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3-Chloro-5H-pyrrolo[2,3-b]pyrazine

CAS No. 1111638-10-8

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