Hexachloroethane → 2-(2-phenoxyquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one

HRID 1055995

Reaktionsgleichung

Reaktionsgleichung von HRID 1055995
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl.[OH:35][C:36]1[C:41]([NH:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[C:49]3[C:54]=2[N:53]=[C:52]([O:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:51]=[CH:50]3)=O)=[C:40]([OH:62])[CH:39]=[CH:38][N:37]=1>C(Cl)Cl>[O:55]([C:52]1[CH:51]=[CH:50][C:49]2[C:54](=[C:45]([C:43]3[O:62][C:40]4[CH:39]=[CH:38][NH:37][C:36](=[O:35])[C:41]=4[N:42]=3)[CH:46]=[CH:47][CH:48]=2)[N:53]=1)[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Komponenten

6

Edukt 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178522456HCID 178522456, Verbindung

Produkt 1

HCID 897821462-(2-phenoxyquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of triphenylphosphine (421 mg, 1.607 mmol), Et3N (597 μl, 4.29 mmol), and perchloroethane (317 mg, 1.339 mmol) in DCM (5357 μl) was stirred at RT for 5 min before a slurry of N-(2,4-dihydroxypyridin-3-yl)-2-phenoxyquinoline-8-carboxamide (200 mg, 0.536 mmol) in DCM (3 ml) was added to make a light yellow solution; this was stirred for 1 h at RT. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 100% DCM to 4% MeOH/DCM) to provide 2-(2-phenoxyquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one (179, 38% yield over two steps) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 6.46 (d, J=7.04 Hz, 1H) 7.22-7.30 (m, 2H) 7.36-7.47 (m, 5H) 7.55 (t, J=7.73 Hz, 1H) 7.95 (d, J=7.24 Hz, 1H) 8.22 (d, J=8.80 Hz, 1H) 8.64 (d, J=6.26 Hz, 1H) 12.51 (br. s., 1H). MS (ESI, pos. ion) m/z: 356.1 (M+1).

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was then concentrated onto silica gel
  3. customchromatographically purified (silica gel, 100% DCM to 4% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a28f1b1b4afe499e9a1578623ed1c0cf
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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