3-((4-Fluorophenyl)aminocarbonyl)benzeneboronic acid → N-(4-Fluoro-phenyl)-3-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzamide

HRID 1470379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470379
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[O:10][C:3]=12.[F:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]2[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=2)=[O:32])=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:31](=[O:32])[C:33]2[CH:34]=[CH:35][CH:36]=[C:37]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]5[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=5)[O:10][C:3]=34)[CH:38]=2)=[CH:28][CH:29]=1

Komponenten

3

Edukt 2

HCID 27828943-((4-Fluorophenyl)aminocarbonyl)benzeneboronic acidHCID 667789647-Chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine

Produkt 1

HCID 56848876N-(4-Fluoro-phenyl)-3-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzamide

Versuchsvorschrift

The title compound was prepared by procedure C using 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine (45.00 mg; 0.14 mmol; 1.00 eq.) instead of 7-chloro-2-iodo-furo[3,2-b]pyridine, and 3-(4-fluorophenyl)aminocarbonyl-phenylboronic acid (40.10 mg; 0.15 mmol; 1.10 eq.) instead of 4-fluorophenylboronic acid and was obtained as a white solid (57 mg, 81%). (HPLC (method F): 87%, RT: 4.33 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 10.51 (s, 1H), 8.96 (s, 1H), 8.67-8.58 (m, 1H), 8.34 (d, J=7.4, 1H), 8.15 (d, J=7.4, 1H), 7.88-7.74 (m, 5H), 7.38 (s, 2H), 7.24 (t, J=7.8, 2H), 3.87 (s, 6H), 3.77-3.68 (m, 3H); MS (m/z) 499 [M+H]+, RT: 4.3 min.

Quellen und Nachweise

ORD-Eintrag
ord-60ab0c75b7b94470b88fdc4f258da28c
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006440B2

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