関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 5-bromo-N-(2-chlorophenyl)thiophene-2-carboxamide | HCID 3508396 | — |
| 反応物 | 5-Chloro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole | HCID 66778733 | — |
| 反応物 | Brine ethyl acetate | HCID 131718255 | — |
| 触媒 | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2-chlorophenyl)carboxamide | HCID 56847660 | 33.2% |
反応手順
A mixture of (5-bromo(2-thienyl))-N-(2-chlorophenyl)carboxamide (7) (25 mg, 0.08 mmol), 2-(5-chloro-2-methylbenzoxazol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4) (23 mg, 0.08 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. The isolated crude product was re-purified on prep HPLC to furnish 10.7 mg of [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2-chlorophenyl)carboxamide (8) as white solid (yield: 33.1%; purity>95%). LC-MS: calcd. for C19H12Cl2N2O2S: 404 (M+1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09079891B2 |
|---|
| 出典データセット | uspto-grants-2015_07 |
|---|
| ORD ID | ord-71a236e0142f4537ab7bcaf566e61918 |
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| 出典メモ | uspto-grants-2015_07 |
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