HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1619251Generated: October 25, 2026
(5-Chloro-2-methoxypyridin-4-yl)boronic acid → 6-(5-Chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole
https://huagongshe.com/reaction/1619251
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | (5-Chloro-2-methoxypyridin-4-yl)boronic acid | HCID 11030558 | — |
| Reactant | 6-Bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole | HCID 59588803 | — |
| Reactant | HCID 178476685 | HCID 178476685 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-(5-Chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole | HCID 23728892 | 6% |
Reaction Steps
To a solution of 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (500 mg, 1.48 mmol) and 5-chloro-2-methoxypyridin-4-yl-4-boronic acid (334 mg, 1.78 mmol) in DMF (20 mL) was added PdCl2(dppf) (108 mg, 0.148 mmol), followed by CH3COOK (581 mg, 5.92 mmol). The mixture was heated at 80° C. for 2 h, filtered and the volatiles evaporated. Water (5 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by the preparative HPLC to give 35 mg (6%) of 6-(5-chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole as a trifluoroacetate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772285B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-2e0b9b81fdb6413f9536dd0bb24ad3f6 |
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| Source note | uspto-grants-2014_07 |
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