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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 240866Generated: October 30, 2026

Dimethylformamide → 6-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

https://huagongshe.com/reaction/240866

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant(4-Methoxyphenyl)boronic acidHCID 201262—
Reactant6-(3-bromo-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineHCID 50991545—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product6-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineHCID 50991927—

Reaction Conditions

Temperature120 °C

Reaction Steps

DMF (5 mL) was added to a mixture of 6-(3-bromo-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (300 mg, 0.710 mmol), K3PO4 (452 mg, 2.13 mmol) and 4-methoxyphenylboronic acid (215 mg, 1.41 mmol) and then the dissolved gas was removed. After adding Pd(PPh3)4 (123 mg, 0.11 mmol), the mixture was stirred at 120° C. for 2 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 was obtained as white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08648089B2
Source datasetuspto-grants-2014_02
ORD IDord-a6ee5f8b9491480597495e20344b4a7b
Source noteuspto-grants-2014_02