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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2192269Generated: October 31, 2026

Dimethylformamide → ethyl 4-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)benzoate

https://huagongshe.com/reaction/2192269

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant4-Ethoxycarbonylphenylboronic acidHCID 2734350—
Reactant6-(3-bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineHCID 50991547—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Productethyl 4-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)benzoateHCID 5099184429.9%

Reaction Conditions

Temperature100 °C

Reaction Steps

DMF (5 mL) was added to a mixture of 6-(3-bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (200 mg, 0.49 mmol), K3PO4 (312 mg, 0.885 mmol) and 4-(ethoxycarbonyl)phenylboronic acid (143 mg, 0.74 mmol) and then the dissolved gas was removed. After adding Pd(PPh3)4 (85 mg, 0.075 mmol), the mixture was stirred at 100° C. for 4 hours. After adding ethyl acetate and water and 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 (70 mg) was obtained as white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08329708B2
Source datasetuspto-grants-2012_12
ORD IDord-fed1be0ee588484aab30d2ecea08bad7
Source noteuspto-grants-2012_12