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

HRID 1010846

반응식

HRID 1010846 반응식
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

참가 물질

7

반응물 3

HCID 10796Cesium carbonate2회HCID 592353Methyl 4-aminopyridine-3-carboxylateHCID 211043424-Chloro-6-(5-chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidine

생성물 1

HCID 588659594-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid methyl ester

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-df93fc38a6c74152aef719e729e3c94f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977342B2

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