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

HRID 1053507

Reaktionsgleichung

Reaktionsgleichung von HRID 1053507
I/[CH:2]=[CH:3]/[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I>[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]([O:4]/[CH:3]=[CH:2]/[N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 798IndoleHCID 10796Cesium carbonateHCID 89873752(E)-4-((2-Iodovinyl)oxy)-1,1'-biphenyl

Produkt 1

HCID 89873720(E)-1-(2-([1,1'-Biphenyl]-4-yloxy)vinyl)-1H-indoleAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe compound 9 was prepared
  2. customto give crude product which
  3. customwere purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a07f4b7584ae45d89e0479383454e1fe
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393306B2

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