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

참여 물질

역할	이름	HCID	투입량
반응물	Sodium Carbonate	HCID 10340	—
반응물	Tri-o-tolylphosphine	HCID 80271	—
반응물	2-Chloropyridine-4-boronic acid, pinacol ester	HCID 5103408	—
반응물	5-(2-Chloro-quinazolin-4-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester	HCID 57832721	—
촉매	palladium(II) acetate	HCID 167845	—
용매	Dichloromethane	HCID 6344	—
용매	1,2-Dimethoxyethane	HCID 8071	—
생성물	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	—

반응 조건

온도	80 °C

반응 단계

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]+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07582631B2
출처 데이터셋	uspto-grants-2009_09
ORD ID	ord-bcdf025d864e487690ea336c7565ef18
출처 메모	uspto-grants-2009_09