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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 85093Generated: October 30, 2026

Sodium Carbonate → 4-{2-Methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-thiazol-2-ylamine

https://huagongshe.com/reaction/85093

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1-Methyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazineHCID 46739039—
Reactant4-(5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamineHCID 86691667—
CatalystHCID 178418476HCID 178418476—
SolventAcetonitrileHCID 6342—
Product4-{2-Methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-thiazol-2-ylamineHCID 54764995—

Reaction Conditions

Temperature175 °C

Reaction Steps

In a personal chemistry microwave reaction vial 4-(5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine (0.2 g, 0.64 mmol) and 1-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperazine (0.23 g, 0.71 mmol), bis(triphenylphosphine)-palladium(II) dichloride (0.004 g, 0.006 mmol) in acetonitrile (2 mL), and 1 M Na2CO3 (2 mL) were added. The resulting mixture was de-gassed with N2 for 10 min, after which it was heated at 175° C. for 30 min in a Personal Chemistry Optimizer. The mixture was diluted with DMF (3 mL), and concentrated in vacuo and purified on silica gel column using dichloromethane and methanol to afford 4-{2-Methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-thiazol-2-ylamine.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846909B2
Source datasetuspto-grants-2014_09
ORD IDord-e1aedcd281ce4b508a5f5a2471061f49
Source noteuspto-grants-2014_09