HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 81355Generated: October 27, 2026
Cesium carbonate → benzyl 2-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoate
https://huagongshe.com/reaction/81355
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | 7-(2,5-Dichloro-pyrimidin-4-yloxy)-2-methyl-2,3-dihydro-isoindol-1-one | HCID 58522554 | — |
| Reactant | Benzyl 4-amino-2-chloro-5-methoxy-benzoate | HCID 58522567 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | benzyl 2-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoate | HCID 58522534 | — |
Reaction Steps
7-(2,5-dichloro-pyrimidin-4-yloxy)-2-methyl-2,3-dihydro-isoindol-1-one (0.10 g), benzyl 4-amino-2-chloro-5-methoxy-benzoate (0.28 g), Pd2dba3 (18 mg), X-Phos (37 mg) and Cs2CO3 are weighed into a microwave vial and argon flushing is carried out. Then toluene (1 mL) and NMP (50 μL) are added, argon flushing is carried out again and the mixture is stirred for 5 min at 150° C. in the microwave. For working up the mixture is diluted with ACN (20 mL) and combined with Isolute (Separtis GmbH). The solvent is eliminated in vacuo and then purified by preparative HPLC. (IC50=53 nmol)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08846689B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-20943953e03d445aab920ef6e333b89c |
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| Source note | uspto-grants-2014_09 |
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