Toluene → Ethyl 6-(4-isopropylthiazol-2-ylamino)-4-phenoxynicotinate

HRID 910967

Reaktionsgleichung

Reaktionsgleichung von HRID 910967
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.[CH:20]([C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1)([CH3:22])[CH3:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.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>[CH:20]([C:23]1[N:24]=[C:25]([NH:28][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:26][CH:27]=1)([CH3:22])[CH3:21]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amineHCID 54487232Ethyl 6-chloro-4-phenoxynicotinate

Produkt 1

HCID 24826427Ethyl 6-(4-isopropylthiazol-2-ylamino)-4-phenoxynicotinateAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Using the method of Example 3, Step B, ethyl 6-chloro-4-phenoxynicotinate (4.296 g, 15.47 mmol), 4-isopropylthiazol-2-amine (2 g, 14.06 mmol), potassium phosphate (3.283 g, 15.47 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.3219 g, 0.3516 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.2238 g, 0.3867 mmol) were reacted in water (15 mL) and toluene (40 mL) to afford the desired product (4.447 g, 74.22% yield) as a yellow solid. 1H NMR (DMSO), 11.36 (s, 1H), 8.72 (s, 1H), 7.49 (m, 2H), 7.30 (m, 1H), 7.17 (m, 1H), 7.15 (m, 1H), 6.59 (m, 2H), 4.24 (q, 2H), 2.81 (m, 1H), 1.25 (t 3H), 1.15 (d, 6H); Mass spectrum (apci) m/z=384 (100) (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-f3f5208676ac4c7992cd47bf801ad103
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

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