HRID2092293

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CNc1ncc2cc(B3OC(C)(C)C(C)(C)O3)ccc2n1

HCID16086139

N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine

C15H20BN3O2

结构：Cc1ccc(C(=O)Nc2cccc(OC(C)C)c2)c(F)c1I

HCID58829750

未命名化合物

PRODUCTS

生成物

结构：CNc1ncc2cc(-c3c(C)ccc(C(=O)Nc4cccc(OC(C)C)c4)c3F)ccc2n1

HCID58829058

未命名化合物

收率 57.1%

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID8071

未命名化合物

PROCEDURE

实验过程

A mixture of 2-fluoro-3-iodo-N-(3-isopropoxyphenyl)-4-methylbenzamide (630 mg, 1525 μmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (522 mg, 1830 μmol) and sodium carbonate (2 M aqueous solution) (1525 μL, 3049 μmol) in DME (25 mL) was flushed with nitrogen and then tetrakis(triphenylphosphine)palladium (0) (176 mg, 152 μmol) was added. The mixture was refluxed for 24 h and thne cooled to RT. Solvent was removed in vacuo and the residue was purified by flash chromatography eluting with EtOAc/hexane (25-60%) to give the title compound (387 mg, 57%). MS (M+H)+ 445.

WORKUP

后处理

customwas flushed with nitrogen
temperatureThe mixture was refluxed for 24 h
customSolvent was removed in vacuo
customthe residue was purified by flash chromatography
washeluting with EtOAc/hexane (25-60%)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e92b329307f5445286d8a336adf92398
来源数据集: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08440674B2
来源说明: uspto-grants-2013_05

反应 SMILES

[F:1][C:2]1[C:20](I)=[C:19]([CH3:22])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([CH3:16])[CH3:15])[CH:8]=1)=[O:5].[CH3:23][NH:24][C:25]1[N:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:31]=2)[N:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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]>[F:1][C:2]1[C:20]([C:30]2[CH:31]=[C:32]3[C:27](=[CH:28][CH:29]=2)[N:26]=[C:25]([NH:24][CH3:23])[N:34]=[CH:33]3)=[C:19]([CH3:22])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([CH3:16])[CH3:15])[CH:8]=1)=[O:5]