HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 240861Generated: October 31, 2026
Dimethylformamide → ethyl 4-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)benzoate
https://huagongshe.com/reaction/240861
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Ethoxycarbonylphenylboronic acid | HCID 2734350 | — |
| Reactant | 6-(3-bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine | HCID 50991547 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | ethyl 4-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)benzoate | HCID 50991844 | 29.9% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08648089B2 |
|---|
| Source dataset | uspto-grants-2014_02 |
|---|
| ORD ID | ord-9ef9dca20f4c4470bc1624e81091d3df |
|---|
| Source note | uspto-grants-2014_02 |
|---|