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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 624247Generated: November 1, 2026

Methanol → HCID 68752610, compound

https://huagongshe.com/reaction/624247

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantCesium carbonateHCID 10796—
Reactant4-[(tert-Butoxycarbonyl)amino]cyclohex-1-en-1-yl trifluoromethanesulfonateHCID 59832199—
ReactantHCID 68753732HCID 68753732—
CatalystHCID 178418807HCID 178418807—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductHCID 68752610HCID 68752610—

Reaction Conditions

Temperature80 °C

Reaction Steps

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxamide (1.692 g, 4.63 mmol), 4-(tert-butoxycarbonylamino)cyclohex-1-enyl trifluoromethanesulfonate (1.6 g, 4.63 mmol) and cesium carbonate (3.77 g, 11.58 mmol) were suspended in terahydrofuran (30 ml), methanol (5.00 ml) and water (15.00 ml). Nitrogen was bubbled throught the solution for 10 min when PdCl2(dppf)-dichloromethane adduct (0.189 g, 0.232 mmol) was added and the mixture was heated to 80° C. for 7 h. After dilution with ethyl acetate and brine, the separated aqueous layer was extracted several times with ethyl acetate and the combined organic layers were dried over magnesium sulfate, filtered and concentrated. Flash chromatography provided the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09302989B2
Source datasetuspto-grants-2016_04
ORD IDord-c62184a3dad34bc1b9102857b07f4c4b
Source noteuspto-grants-2016_04