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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 240863Generated: October 30, 2026

Dimethylformamide → 3-(4-methoxyphenyl)-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

https://huagongshe.com/reaction/240863

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant(4-Methoxyphenyl)boronic acidHCID 201262—
Reactant3-bromo-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indoleHCID 50991543—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product3-(4-methoxyphenyl)-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indoleHCID 5099192469.5%

Reaction Conditions

Temperature100 °C

Reaction Steps

DMF (2 mL) was added to a mixture of 3-bromo-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (130 mg, 0.295 mmol), K3PO4 (188 mg, 0.885 mmol) and 4-methoxyphenylboronic acid (90 mg, 0.59 mmol) and then the dissolved gas was removed. After adding Pd(PPh3)4 (68 mg, 0.055 mmol), the mixture was stirred at 100° C. for 4 hours. After adding ethyl acetate and water and then filtering using a diatomite pad, the organic layer was separated and the aqueous layer was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:4-1:1). The target compound (96 mg) was obtained as white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08648089B2
Source datasetuspto-grants-2014_02
ORD IDord-0b449199b380471681848152bcba82f8
Source noteuspto-grants-2014_02