Dichloromethane → 1-Phenyltriazolylmethyl-3-hydroxypyridine-2-one

HRID 539526

Reaktionsgleichung

Reaktionsgleichung von HRID 539526
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[N:15]=[N:16][NH:17][CH:18]=3)=[C:9]([O:19]C)[C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(Cl)Cl>>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[N:15]=[N:16][NH:17][CH:18]=3)=[C:9]([OH:19])[C:8]2=[O:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 1784876421-Phenyltriazolylmethyl-3-methoxypyridine-2-one

Produkt 1

HCID 1785168861-Phenyltriazolylmethyl-3-hydroxypyridine-2-oneAusbeute 61,1 %

Versuchsvorschrift

Reaction of 151a (0.212 g, 0.75 mmol) and 1M BBr3 in CH2Cl2 (1.5 equiv) within 48 h as described for the synthesis of 148a gave compound 152a (0.123 g, 61%) as light brown solid. 1H NMR (DMSO-d6, 400 MHz) δ 5.27 (2H, s), 6.13 (1H, t, J=6.4), 6.67 (1H, d, J=7.2), 7.30 (1H, d, J=5.6), 7.45-7.49 (1H, m), 7.57 (2H, t, J=7.6), 7.87 (2H, d, J=8.0), 8.73 (1H, s), 9.08 (1H, s); 13C NMR (101 MHz, CDCl3) δ 136.59, 129.60, 128.94, 122.29, 120.62, 107.99, 29.29. (quaternary carbons were not seen). HRMS (EI) calcd for C14H12N4O2 [M]+ 268.0960. found 268.0967.

Quellen und Nachweise

ORD-Eintrag
ord-5330f9f182aa4b03843cfa55a6973f0d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871728B2

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