1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Name: 1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
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CAS No. 1644629-23-1
Cat. No. CS-0052443
Molecule weight258.12
Purity≥95%
MDL No.None

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1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine|CS-0052443

Structure of 1644629-23-1

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General Information

CAS No. 1644629-23-1
Cat. No. CS-0052443
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₉BN₂O₂
Molecular Weight 258.12
Synonym(s) 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
SMILES CN1C=CC2=C(C=CN=C12)B1OC(C)(C)C(C)(C)O1

Description

1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is a bench-stable boronate ester featuring a pyrrolopyridine core with enhanced solubility and reactivity in cross-coupling applications. This compound integrates seamlessly into Suzuki-Miyaura reactions, enabling efficient C–C bond formation under mild conditions. The tetramethylboronate moiety ensures high functional group tolerance and stability during handling.

Application

1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient C–C bond formation with aryl and heteroaryl halides. The boronate ester functionality exhibits excellent stability under ambient conditions, facilitates straightforward purification, and tolerates a range of functional groups. Its structural motif is well-established in the synthesis of bioactive heterocycles and pharmaceutical intermediates.

Safety Information

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

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Computational Chemistry Data

TPSA 36.28
LogP 1.8725
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

CAS No. 1644629-23-1

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