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

HRID 1056000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056000
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.CCN(CC)CC.[Cl:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[C:39]([C:46]([NH:48][C:49]3[C:50]([OH:56])=[N:51][CH:52]=[CH:53][C:54]=3[OH:55])=O)[CH:40]=[CH:41][CH:42]=2)[N:37]=1>C(Cl)Cl>[Cl:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[C:39]([C:46]3[O:55][C:54]4[CH:53]=[CH:52][NH:51][C:50](=[O:56])[C:49]=4[N:48]=3)[CH:40]=[CH:41][CH:42]=2)[N:37]=1

Komponenten

6

Edukt 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178522455HCID 178522455, Verbindung

Produkt 1

HCID 897823932-(2-chloroquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of triphenylphosphine (381 mg, 1.454 mmol), perchloroethane (287 mg, 1.212 mmol), and Et3N (540 μl, 3.88 mmol) in DCM (4846 μl) was stirred at RT for 1 h. The yellow solution was transferred to a flask containing solid 2-chloro-N-(2,4-dihydroxypyridin-3-yl)quinoline-8-carboxamide (153 mg, 0.485 mmol); this was stirred at RT for 1 h. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(2-chloroquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one (181, >99% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.92 (d, J=7.04 Hz, 1H) 7.53 (t, J=6.65 Hz, 1H) 7.77 (d, J=8.61 Hz, 1H) 7.84-7.90 (m, 1H) 8.35 (dd, J=8.22, 1.37 Hz, 1H) 8.43 (dd, J=7.24, 1.37 Hz, 1H) 8.64 (d, J=8.61 Hz, 1H) 11.89 (br. s., 1H). MS (ESI, pos. ion) m/z: 298.1 (M+1).

Aufarbeitung

  1. customThe yellow solution was transferred to a flask
  2. customPurification by silica gel (100% DCM to 4% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-60dc0969c4cc429fac8ce1ff358f2a39
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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