HRID1052485

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CN(c1cccc(B2OC(C)(C)C(C)(C)O2)c1)S(C)(=O)=O

HCID57416160

N-Methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide

C14H22BNO4S

结构：Cc1ccn2nc([C@H](C)Nc3ncnc4c3c(Br)cn4COCC[Si](C)(C)C)n(-c3ccccc3)c(=O)c12

HCID131736122

未命名化合物

PRODUCTS

生成物

结构：Cc1ccn2nc([C@H](C)Nc3ncnc4c3c(-c3cccc(N(C)S(C)(=O)=O)c3)cn4COCC[Si](C)(C)C)n(-c3ccccc3)c(=O)c12

HCID131736167

未命名化合物

收率 93%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1

催化剂HCID178418476

未命名化合物

PROCEDURE

实验过程

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (131 mg, 0.22 mmol) was treated with N-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (170 mg, 0.55 mmol, prepared according to WO 2006015829 A1 20060216), sodium carbonate (62 mg, 0.58 mmols) and bis(triphenylphosphine)palladium(II) dichloride (55 mg, 0.07 mmol) according to the method described in Preparation 62. The residue was purified using SP1® Purification System (0% to 100%, hexane-ethyl ether) to give 143 mg (92% yield) of the title compound. Purity 99%.

WORKUP

后处理

customdescribed in Preparation 62
customThe residue was purified
customSP1® Purification System (0% to 100%, hexane-ethyl ether)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d9d2540e396448858e2e7dea33faa922
来源数据集: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09388189B2
来源说明: uspto-grants-2016_07

反应 SMILES

Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=1.[CH3:39][N:40]([C:45]1[CH:50]=[CH:49][CH:48]=[C:47](B2OC(C)(C)C(C)(C)O2)[CH:46]=1)[S:41]([CH3:44])(=[O:43])=[O:42].C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:39][N:40]([C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:2]2[C:10]3[C:9]([NH:11][C@H:12]([C:14]4[N:19]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:18](=[O:26])[C:17]5=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]5[N:15]=4)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=2)[CH:46]=1)[S:41]([CH3:44])(=[O:42])=[O:43]