Potassium Carbonate → 6-(5-Chloropyridin-3-yl)-5'-methylspiro[chroman-4,2'-imidazol]-4'-amine

참여 물질

역할	이름	HCID	투입량
반응물	Potassium Carbonate	HCID 11430	—
반응물	5-Chloropyridine-3-boronic acid	HCID 20111877	—
반응물	6-Bromo-5'-methylspiro[chromane-4,2'-imidazol]-4'-amine	HCID 67979605	—
촉매	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
용매	1,4-Dioxane	HCID 31275	—
생성물	6-(5-Chloropyridin-3-yl)-5'-methylspiro[chroman-4,2'-imidazol]-4'-amine	HCID 57384615	64.3%

반응 조건

온도	130 °C

반응 단계

6-Bromo-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (60 mg, 0.20 mmol, Intermediate 4), 5-chloropyridin-3-ylboronic acid (62 mg, 0.40 mmol) and 2M K2CO3 (aq, 0.20 mL, 0.41 mmol) were mixed in dioxane (5 mL) and degassed by passing nitrogen through for 5 min. Then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (8 mg, 10 μmol) was added and the mixture was heated in a microwave oven at 130° C. for 1 h. Purification by preparative chromatography HPLC gave the title compound (42 mg, 63% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.17 (m, 2 H), 2.37 (s, 3 H), 4.59 (m, 2 H), 5.04 (br s, 2 H), 6.73 (d, 1 H), 7.01 (d, 1 H), 7.34 (dd, 1 H), 7.70 (m, 1 H), 8.45 (m, 1 H), 8.55 (m, 1 H); MS (ES+) m/z 327 [M+H]+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08865911B2
출처 데이터셋	uspto-grants-2014_10
ORD ID	ord-8018cd3311a54020b1ab72afc0ba0527
출처 메모	uspto-grants-2014_10