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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1053507Erstellt: 26. Oktober 2026

Indole → (E)-1-(2-([1,1'-Biphenyl]-4-yloxy)vinyl)-1H-indole

https://huagongshe.com/reaction/1053507

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktIndoleHCID 798—
EduktCesium carbonateHCID 10796—
Edukt(E)-4-((2-Iodovinyl)oxy)-1,1'-biphenylHCID 89873752—
KatalysatorCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
Produkt(E)-1-(2-([1,1'-Biphenyl]-4-yloxy)vinyl)-1H-indoleHCID 8987372087%

Reaktionsschritte

The compound 9 was prepared following the procedure described for 5 with 4 (0.32 g, 1 mmol, 1 eq), indole (0.14 g, 1.2 mmol, 1.2 eq), Cs2CO3 (0.81 g, 2.5 mmol, 2.5 eq), CuI (0.095 g, 0.5 mmol, 0.5 eq) and L2 (0.097 g, 0.5 mmol, 0.5 eq) at 70° C. for 12 h to give crude product which were purified by silica gel column chromatography using ethyl acetate-hexane (9:95) to afford compound 9 as white crystals (0.27 g, 87%): mp 140-142° C. 1H NMR (300 MHz, CDCl3): 7.58-7.46 (m, 6H, HAr), 7.40-7.32 (m, 3H, HAr), 7.25-7.21 (m, 1H, HAr), 7.20-7.14 (m, 2H, HAr), 7.12-7.02 (m, 4H, HAr and H(O)C═(N)CH), 6.55 (d, H, J=3.1 Hz, HAr). 13C NMR (75 MHz, CDCl3): 156.8, 140.4, 136.5, 136.4, 128.9, 128.8, 128.5, 127.1, 126.9, 125.7, 125.6, 121.2, 120.5, 116.5, 115.2, 109.8, 104.0 ppm; IR (cm−1): 3034, 2358, 2338, 1682, 1606, 1515, 1485, 1475, 1462, 1358, 1333, 1322, 1301, 1232, 1202, 1186, 1174, 1134, 1115, 1088, 1031, 1007, 907, 865, 834; HRMS (ESI), Calculated for C22H17NO [M+H]+ 312.1388. Found 312.1381; Elemental analysis Calculated for C22H17NO.0.25H2O: C, 83.65; H, 5.58; N, 4.43. found: C, 83.61; H, 5.65; N, 4.01.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09393306B2
Quelldatensatzuspto-grants-2016_07
ORD IDord-a07f4b7584ae45d89e0479383454e1fe
Quellennotizuspto-grants-2016_07