関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | 3-Aminophenylboronic acid hydrochloride | HCID 2763241 | — |
| 反応物 | 6-Bromo-5-chloro-2-methylbenzoxazole | HCID 58487438 | — |
| 触媒 | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 溶媒 | Hexane | HCID 8058 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 4-(5-Chloro-2-methylbenzoxazol-6-yl)phenylamine | HCID 67467295 | 42% |
反応手順
A mixture of 6-bromo-5-chloro-2-methylbenzoxazole (54) (160 mg, 0.65 mmol), anilin-5-boronic acid hydrochloride salt (55) (135 mg, 1.2 eq), Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (A-Phos) (46 mg, 0.1 mmol) and K3PO4 (165 mg) in 2 ml ACN, 2 ml dioxane and 0.5 ml H2O was bubbled with argon before heated at 85° C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting red solid was dissolved in DCM and subjected to silica gel column purification using 0-60% B (A: hexane; B: 50% EA in hexane) to furnish 70.6 mg 56 as yellow solid (yield: 42%)
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09353099B2 |
|---|
| 出典データセット | uspto-grants-2016_05 |
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| ORD ID | ord-a225d33d61544ebfb79172505de33767 |
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| 出典メモ | uspto-grants-2016_05 |
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