関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Methyl 4-iodobenzoate | HCID 69273 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | 8-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine | HCID 46864069 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | Methyl 4-(8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate | HCID 59198947 | 68.7% |
反応手順
A suspension of 8-bromo-[1,2,4]triazolo[1, 5-a]pyridin-2-amine (2.8 g, 13.2 mmol, 1 equiv), methyl 4-iodobenzoate (3.4 g, 13 mmol, 1.0 equiv), cesium carbonate (8.4 g, 26 mmol, 2.0 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (763 mg, 1.32 mmol, 0.10 equiv), and palladium (II) acetate (300 mg, 1.32 mmol, 0.10 equiv) in dioxane (100 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane (100 mL). The resulting solids were filtered and sequentially rinsed with water (3×50 mL) and methanol (2×20 mL). The solids were dried in vacuo to afford methyl 4-(8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (3.1 g). 1H NMR (400 MHz, DMSO-d6), δ: 10.42 (s, 1H), 8.87 (m, 1H), 7.93 (m, 1H), 7.92 (d, J=8.8 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H), 7.00 (dd, J=7.4, 6.9 Hz, 1H), 3.81 (s, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09434732B2 |
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| 出典データセット | uspto-grants-2016_09 |
|---|
| ORD ID | ord-70c2d067330c483b97778b370d71ce27 |
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| 出典メモ | uspto-grants-2016_09 |
|---|
