Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylborane | HCID 7357 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 22144554 | HCID 22144554 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 9970412 | HCID 9970412 | 38.3% |
Reaction Steps
To a solution of 6-methoxy-2-(2-bromo-3-methoxy-phenyl)-benzothiazole (0.182, 0.52 mmol) in dry DMF (3 mL) was added cesium carbonate (0.51 g, 1.57 mmol), triethylborane (0.58 mL, 1M in THF, 0.58 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride dichloromethane (18 mg, 0.022 mmol). The mixture was heated to 50° C. for 24 h, then cooled to room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethylacetate. Combined ethylacetate were washed with brine, concentrated. After chromatographic purification gave 6-methoxy-2-(3-methoxy-phenyl)-benzothiazole (54 mg, 38% yield) as a white solid. Mass spec: MH+=272.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07045539B2 |
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| Source dataset | uspto-grants-2006_05 |
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| ORD ID | ord-028ee8b0118f4ab2b5262db55e64423a |
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| Source note | uspto-grants-2006_05 |
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