Water → HCID 24825877, Verbindung

HRID 910916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910916
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Si:8]([O:15][C:16]1[CH:17]=[C:18]([S:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[CH:24]=2)[CH:19]=[CH:20][CH:21]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Si:8]([O:15][C:16]1[CH:17]=[C:18]([S:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:7][C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[CH:24]=2)[CH:19]=[CH:20][CH:21]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Komponenten

8

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 866347184-(3-(Tert-butyldimethylsilyloxy)phenylthio)-2-chloropyridine

Produkt 1

HCID 24825877HCID 24825877, VerbindungAusbeute 31,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (9.20 mL, 3.68 mmol), 4-(3-(tert-butyldimethylsilyloxy)phenylthio)-2-chloropyridine (1.42 g, 4.05 mmol), potassium phosphate (0.859 g, 4.05 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.0842 g, 0.0920 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0585 g, 0.101 mmol) were reacted in toluene (10 mL) and water (3 mL) to afford N-(4-(3-(tert-butyldimethylsilyloxy)phenylthio)pyridin-2-yl)-4-methylthiazol-2-amine (0.500 g, 28.5% yield) as yellow solid. 1H NMR (CDCl3) δ 8.08 (d, 1H), 7.27 (t, 1H), 7.12 (dt, 1H), 7.00 (t, 1H), 6.90 (m, 1H), 6.56 (dd, 1H), 6.47 (d, 1H), 6.32 (d, 1H), 2.23 (d, 3H), 0.96 (s, 9H), 0.18 (s, 6H).

Quellen und Nachweise

ORD-Eintrag
ord-2b0d4ff1920c40cf84b884a13fa14a34
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

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