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

HRID 1010846

反応式

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

参加物

反応条件

温度: 90 °C

実験手順

4-Chloro-6-(5-chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidine (prepared by method used for compound of formula (43) (298 mg, 1 mmole) was dissolved in dioxane (4 ml), and BINAP (4.67 mg, 0.0075 mmole), 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) were added to the mixture and heated to 90° C. overnight. Dioxane was removed under vacuum and the residue was triturated with ethyl acetate (5 ml) and the product was isolated by filtration. 525 mg of solid were obtained which also contained cesium carbonate as by-product.

後処理

customDioxane was removed under vacuum
customthe residue was triturated with ethyl acetate (5 ml)
customthe product was isolated by filtration

出典と根拠

ORDレコード: ord-df93fc38a6c74152aef719e729e3c94f
出典データセット: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07977342B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

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