Cesium carbonate → 2,6-Dichloro-4-Cyano-N-{2-[(Cyclopropylcarbonyl)amino]pyridin-4-Yl}benzamide

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	Cyclopropanecarboxamide	HCID 80376	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide	HCID 86648954	—
촉매	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
용매	1,4-Dioxane	HCID 31275	—
생성물	2,6-Dichloro-4-Cyano-N-{2-[(Cyclopropylcarbonyl)amino]pyridin-4-Yl}benzamide	HCID 59618273	40%

반응 조건

온도	140 °C

반응 단계

A mixture of N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (74 mg, 0.20 mmol), cyclopropanecarboxamide (34 mg, 0.40 mmol), Pd2(dba)3 (18 mg, 0.020 mmol), Xantphos (23 mg, 0.040 mmol), Cs2CO3 (131 mg, 0.40 mmol), dioxane (1.2 mL) was heated to 140° C. for 1 hour in a microwave reactor under nitrogen atmosphere. The mixture was filtered through Celite and then conentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford the desired product (30 mg, yield: 40%). 1H NMR (500 MHz, DMSO-d6): δ 11.28 (s, 1H), 10.79 (s, 1H), 8.36-8.24 (m, 4H), 7.47 (m, 1H), 2.00 (m, 1H), 0.81-0.79 (m, 4H). LCMS (ESI) m/z: 375 [M+H+].

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08486950B2
출처 데이터셋	uspto-grants-2013_07
ORD ID	ord-98de4c594b144a25a334c763f4709939
출처 메모	uspto-grants-2013_07