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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2192271Generated: October 31, 2026

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

https://huagongshe.com/reaction/2192271

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 numberUS08329708B2
Source datasetuspto-grants-2012_12
ORD IDord-728b5f0ae6cf43d0834ed6ec49fc1c00
Source noteuspto-grants-2012_12