HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1891337Generated: November 1, 2026
Nitrogen → tert-Butyl 3-(3-methylpyridin-2-yl)benzoate
https://huagongshe.com/reaction/1891337
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Methanesulfonic Acid | HCID 6395 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-Bromo-3-methylpyridine | HCID 220832 | — |
| Reactant | (3-((Tert-butoxy)carbonyl)phenyl)boronic acid | HCID 2773299 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | tert-Butyl 3-(3-methylpyridin-2-yl)benzoate | HCID 57516851 | 82% |
Reaction Steps
2-Bromo-3-methylpyridine (1.0 eq) is dissolved in toluene (12 vol). K2CO3 (4.8 eq) is added followed by water (3.5 vol) and the mixture heated to 65° C. under a stream of N2 for 1 hour. 3-(t-Butoxycarbonyl)phenylboronic acid (1.05 eq) and Pd(dppf)Cl2.CH2Cl2 (0.015 eq) are then added and the mixture is heated to 80° C. After 2 hours, the heat is turned off, water is added (3.5 vol) and the layers are allowed to separate. The organic phase is then washed with water (3.5 vol) and extracted with 10% aqueous methanesulfonic acid (2 eq MsOH, 7.7 vol). The aqueous phase is made basic with 50% aqueous NaOH (2 eq) and extracted with EtOAc (8 vol). The organic layer is concentrated to afford crude tert-butyl-3-(3-methylpyridin-2-yl)benzoate (82%) that is used directly in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08507534B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-ae3c1cffc1ab4d53806301f8868a08e6 |
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| Source note | uspto-grants-2013_08 |
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