HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1524225Generated: October 27, 2026
Sodium Carbonate → [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2,6-difluorophenyl)carboxamide
https://huagongshe.com/reaction/1524225
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-bromo-N-(2,6-difluorophenyl)thiophene-2-carboxamide | HCID 51970844 | — |
| Reactant | 5-Chloro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole | HCID 66778733 | — |
| Reactant | Brine ethyl acetate | HCID 131718255 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2,6-difluorophenyl)carboxamide | HCID 68062154 | 69.2% |
Reaction Steps
A mixture of (5-bromo(2-thienyl))-N-(2,6-difluorophenyl)carboxamide (25 mg, 0.08 mmol), 2-(5-chloro-2-methylbenzoxazol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4) (29 mg, 0.1 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 12 mg) and sodium carbonate (32 mg) in 0.5 ml DME, 0.5 ml EtOH and 0.25 ml water was heated under Ar in microwave reactor at 110° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to silica gel flash column chromatography to furnish 22.4 mg of [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2,6-difluorophenyl)carboxamide (11) as yellow solid (yield: 55.3%; purity>95%). LC-MS: calcd. for C19H11ClF2N2O2S: 405 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09079891B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-b363efa132b84d4ba94f06a3ef893146 |
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| Source note | uspto-grants-2015_07 |
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