化工社化工社 化学情報印刷レポート · 研究参考用
HRID 729532作成日：2026年10月26日
Sodium Carbonate → 5-[2-(2-Chloro-pyridin-4-yl)-quinazolin-4-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/729532
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Tri-o-tolylphosphine | HCID 80271 | — |
| 反応物 | 2-Chloropyridine-4-boronic acid, pinacol ester | HCID 5103408 | — |
| 反応物 | 5-(2-Chloro-quinazolin-4-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester | HCID 57832721 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | 5-[2-(2-Chloro-pyridin-4-yl)-quinazolin-4-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester | HCID 86600306 | — |
反応手順
A solution of 5-(2-chloro-quinazolin-4-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.145 g, 0.4 mmol) in DME (2 mL) under nitrogen were added palladium acetate (0.0045 g, 0.02 mmol), tri-o-tolylphosphine (0.015 g, 0.048 mmol), and 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (0.19 g, 0.8 mmol), followed by 2M Na2CO3 (0.6 mL, 1.2 mmol). The resulting mixture was heated at 80° C. for 20 h. The reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate and brine and dried (MgSO4). Flash chromatography of the crude product mixture with 25:10:65, 35:10:55, and 50:10:40 EtOAc-CH2Cl2-Hexane gave the title compound. MS (ES+): 438.2 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07582631B2 |
|---|
| 出典データセット | uspto-grants-2009_09 |
|---|
| ORD ID | ord-bcdf025d864e487690ea336c7565ef18 |
|---|
| 出典メモ | uspto-grants-2009_09 |
|---|
