HRID12277

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID77531

2,4-Dichloropyrimidine

C4H2Cl2N2

HCID522689

Potassium fluoride

结构：C[Si](C)(C)CCOCn1nc(B(O)O)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O

HCID68680596

未命名化合物

PRODUCTS

生成物

结构：C[Si](C)(C)CCOCn1nc(-c2ccnc(Cl)n2)cc(-c2nc3ccc(C(F)(F)F)cc3n2COCC[Si](C)(C)C)c1=O

HCID86611607

未命名化合物

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HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

6-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid, 2,4-di-chloropyrimidine, potassium fluoride and tris(dibenzylideneacetone)dipalladium(0) are dissolved in dry THF and degassed with argon for 10 minutes. Tri-tert-butyl-phosphonium tetrafluoroborate is added, and the reaction mixture is stirred at room temperature for 16 hours. LC-MS analysis shows complete conversion. The solvent is removed in a rotary evaporator, the residue is dissolved in DMF and the crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid)). MS (ES+) m/z 653 (M+H).

WORKUP

后处理

customdegassed with argon for 10 minutes
additionTri-tert-butyl-phosphonium tetrafluoroborate is added
customThe solvent is removed in a rotary evaporator
dissolutionthe residue is dissolved in DMF
customthe crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-de6193c7d6a84e4199662d280a686708
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07727989B2
来源说明: uspto-grants-2010_06

反应 SMILES

[O:1]=[C:2]1[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:6]=[C:5](B(O)O)[CH:4]=[C:3]1[C:19]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22]2[CH:32]=[C:33]([C:36]([F:39])([F:38])[F:37])[CH:34]=[CH:35][C:21]=2[N:20]=1.[Cl:40][C:41]1[N:46]=[C:45](Cl)[CH:44]=[CH:43][N:42]=1.[F-].[K+]>C1COCC1.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]>[Cl:40][C:41]1[N:46]=[C:45]([C:5]2[CH:4]=[C:3]([C:19]3[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:30])[CH3:31])[C:22]4[CH:32]=[C:33]([C:36]([F:39])([F:38])[F:37])[CH:34]=[CH:35][C:21]=4[N:20]=3)[C:2](=[O:1])[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[N:6]=2)[CH:44]=[CH:43][N:42]=1