関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 6-Bromoisoquinoline | HCID 313681 | — |
| 反応物 | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2774010 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 溶媒 | Sodium Bicarbonate | HCID 516892 | — |
| 生成物 | 6-(1H-pyrazol-4-yl)isoquinoline | HCID 57950612 | 37.8% |
反応手順
A mixture of 6-bromoisoquinoline (500 mg, 2.40 mmol) (commercially available from Kalexsyn Product List (Order Number 2003-005)), pyrazole-4-boronic acid pinacol ester (560 mg, 2.88 mmol) (commercially available from Acros Organics (Order Number 38294)), trans-dichlorobis(triphenylphosphine)palladium(II) (118 mg, 0.17 mmol), and sodium carbonate (764 mg, 7.21 mmol) in DME:EtOH:H2O=7:2:3 (4 mL) was heated at 140° C. for 10 minutes in a Biotage Initiator® microwave. After cooling to room temperature, the mixture was diluted with saturated aqueous NaHCO3 and extracted with 25% i-PrOH/CHCl3 (3×). The combined organic layers were dried over Na2SO4, filtered and adsorbed onto silica gel. The residue was purified using column chromatography (acetone/hexanes=0-50%) to provide the product as an off-white solid (177 mg, 37%). LCMS (API-ES) m/z: 196 (M+H+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07897619B2 |
|---|
| 出典データセット | uspto-grants-2011_03 |
|---|
| ORD ID | ord-8faf3a660eaf4decbe9ca28c5bc40927 |
|---|
| 出典メモ | uspto-grants-2011_03 |
|---|
