Water → Ethyl 6-(4-methylthiazol-2-ylamino)-4-phenoxynicotinate

HRID 910962

Reaktionsgleichung

Reaktionsgleichung von HRID 910962
Cl[C:2]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[CH3:20][C:21]1[N:22]=[C:23]([NH2:26])[S:24][CH:25]=1.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>[CH3:20][C:21]1[N:22]=[C:23]([NH:26][C:2]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=2)[S:24][CH:25]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 54487232Ethyl 6-chloro-4-phenoxynicotinate

Produkt 1

HCID 24826421Ethyl 6-(4-methylthiazol-2-ylamino)-4-phenoxynicotinateAusbeute 68,6 %

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, ethyl 6-chloro-4-phenoxynicotinate (12.0 g, 43.4 mmol), 4-methylthiazol-2-amine (4.49 g, 39.4 mmol), potassium phosphate (9.20 g, 43.4 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.902 g, 0.985 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.627 g, 1.08 mmol) were combined in toluene (100 mL) and water (25 mL) to afford ethyl 6-(4-methylthiazol-2-ylamino)-4-phenoxynicotinate (9.6 g, 67.8% yield) as yellow solid. 1H NMR (CDCl3) δ 8.88 (s, 1H), 7.40 (m, 2H), 7.25 (m, 1H), 7.08 (m, 1H), 7.07 (m, 1H), 6.30 (d, 1H), 6.06 (s, 1H), 4.35 (q, 2H), 2.04 (s, 3H), 1.35 (t, 3H); Mass spectrum (esi) m/z=356 (100)(M+H).

Quellen und Nachweise

ORD-Eintrag
ord-4f471baa8b80411fb6f95f6e13b01d4d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

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