Cesium carbonate → 4-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid methyl ester

HRID 1354313

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[F:15])[N:5]=[C:4]2[O:16][N:17]=[C:18]([CH3:19])[C:3]=12.[CH3:20][O:21][C:22](=[O:30])[C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[N:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][O:21][C:22](=[O:30])[C:23]1[C:28]([NH:29][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=3[F:15])[N:5]=[C:4]3[O:16][N:17]=[C:18]([CH3:19])[C:3]=23)=[CH:27][CH:26]=[N:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

4-Chloro-6-(5-chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidine (Prepared by method used for 0043) (298 mg, 1 mmole) was dissolved in dioxane (4 ml), added BINAP (4.67 mg, 0.0075), 4-Amino-nicotinic acid methyl ester (182 mg, 1.2 mmole), cesium carbonate (456 mg, 1.4 mmole), and Pd2(dba)3 (2.29 mg, 0.0025 mmole) to the mixture and heated to 90° C. overnight. Removed dioxane under vacuum and triturated residue with ethyl acetate (5 ml) and isolated product by filtration. Obtained 525 mg solid which also contained cesium carbonate as byproduct.

Aufarbeitung

customRemoved dioxane under vacuum and triturated residue with ethyl acetate (5 ml)
customisolated product
filtrationby filtration

Quellen und Nachweise

ORD-Eintrag: ord-c36d067062e14c268c718d1fd1340036
Quelldatensatz: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07223766B2

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