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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1053113Generated: October 28, 2026

Water → HCID 90273484, compound

https://huagongshe.com/reaction/1053113

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
Reactant1-Methyl-1H-indole-5-boronic acidHCID 2759867—
ReactantHCID 90273228HCID 90273228—
CatalystHCID 178418397HCID 178418397—
SolventEthyl AcetateHCID 8857—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 90273484HCID 90273484—

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyrazin-2-ylamine (750 mg, 2.65 mmol) and N-methylindole-5-boronic acid (556 mg, 3.18 mmol) in 1,4-dioxane (15.0 mL)/water (5.0 mL) was added Cs2CO3 (1.29 g, 3.97 mmol) at room temperature. The reaction mixture was purged with argon for 30 min. Then Pd(PPh3)4 (153 mg, 0.13 mmol) was added and allowed to stir at 100° C. for 16 h. The reaction mixture was cooled to RT, diluted with EtOAc (20 mL) and washed with water (20 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford crude product. The crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 70-80% EtOAc in Hexane to afford the title compound as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09393248B1
Source datasetuspto-grants-2016_07
ORD IDord-6cc356970c8646b5804078c290307b59
Source noteuspto-grants-2016_07