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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1616033Generated: November 2, 2026

Morpholine → HCID 44539731, compound

https://huagongshe.com/reaction/1616033

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
ReactantCesium carbonateHCID 10796—
ReactantBinap, (A+-)-HCID 634876—
ReactantHCID 44540317HCID 44540317—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventDimethyl sulfoxide methanolHCID 22036561—
ProductHCID 44539731HCID 4453973122.8%

Reaction Conditions

Temperature150 °C

Reaction Steps

5-Bromo-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (35 mg, 0.08 mmol) and morpholine (1 ml, 11.5 mmol) were placed in a microwave vial. Pd2dba3 (4 mg, 0.004 mmol), BINAP (5 mg, 0.008 mmol) and cesium carbonate (40 mg, 0.12 mmol) were added and the mixture was heated at 150° C. for 75 mins under microwave irradiation. The reaction mixture was concentrated in vacuo to give a crude residue that was suspended in 1:1 DMSO/MeOH (1 ml) and filtered to give an orange solution that was purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with MeOH and the solvent removed under a stream of nitrogen to give the title compound (8 mg) as a pale orange solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08765743B2
Source datasetuspto-grants-2014_07
ORD IDord-a135e9b44c7749daa90fd7a9e61f4d87
Source noteuspto-grants-2014_07