HRID1082275

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID31275

1,4-Dioxane

C4H8O2

HCID522689

Potassium fluoride

结构：C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC

HCID619414

Tributyl(1-ethoxyvinyl)stannane

C16H34OSn

结构：Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Br)cc2)cc1

HCID19689478

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccccc2)cc1

HCID19689460

未命名化合物

结构：CC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1

HCID19689469

未命名化合物

结构：CCOC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1

HCID19689528

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：[Cl][Pd][Cl].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1

催化剂HCID6102075

未命名化合物

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A mixture of N-[6-{2-(4-bromophenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (600 mg), (1-ethoxyvinyl)tributyltin (680 mg), bis(triphenylphosphine)palladium (II) chloride (35.5 mg) and dioxane (24 ml) is refluxed for 18 hours. The mixture is diluted with ethyl acetate, and thereto is added 10% aqueous potassium fluoride solution, and the precipitated crystals are removed by filtration. The filtrate is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=5:1~3:1~1:1), and the obtained compounds are each recrystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-{5-(4-methylphenyl)-6-(2-phenoxyethoxy)pyrimidin-4-yl}benzenesulfonamide (Compound A) (42 mg), N-[6-{2-(4-acetylphenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (Compound B) (242 mg) and 4-tert-butyl-N-[6-{2-(4-ethoxycarbonylphenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (Compound C) (58 mg), respectively.

WORKUP

后处理

temperatureis refluxed for 18 hours
customthe precipitated crystals are removed by filtration
extractionThe filtrate is extracted with ethyl acetate
washthe ethyl acetate layer is washed
customdried
concentrationconcentrated to dryness under reduced pressure
customThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=5:1~3:1~1:1)
customeach recrystallized from ethyl acetate/diisopropyl ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cc4e7fdb2826471283a0e37b45a5bc66
来源数据集: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05589478
来源说明: uspto-grants-1996_12

反应 SMILES

Br[C:2]1[CH:38]=[CH:37][C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]=2[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)=[CH:4][CH:3]=1.[CH2:39]([O:41]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:40].O1C[CH2:61][O:60][CH2:59][CH2:58]1.[F-].[K+]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([S:17]([NH:16][C:12]2[C:11]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[C:10]([O:9][CH2:8][CH2:7][O:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:38][CH:37]=3)[N:15]=[CH:14][N:13]=2)(=[O:19])=[O:18])=[CH:25][CH:24]=1)([CH3:29])([CH3:27])[CH3:28].[C:39]([C:2]1[CH:38]=[CH:37][C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]=2[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)=[CH:4][CH:3]=1)(=[O:41])[CH3:40].[C:26]([C:23]1[CH:24]=[CH:25][C:20]([S:17]([NH:16][C:12]2[C:11]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[C:10]([O:9][CH2:8][CH2:7][O:6][C:5]3[CH:37]=[CH:38][C:2]([C:61]([O:60][CH2:59][CH3:58])=[O:41])=[CH:3][CH:4]=3)[N:15]=[CH:14][N:13]=2)(=[O:19])=[O:18])=[CH:21][CH:22]=1)([CH3:29])([CH3:28])[CH3:27]