HRID2408443

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CC(C)(C)OC(=O)Nc1ccc(B2OC(C)(C)C(C)(C)O2)cn1

HCID17750222

tert-Butyl [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]carbamate

C16H25BN2O4

结构：O=C(/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1)NOC1CCCCO1

HCID86621691

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)Nc1ccc(-c2ccc(S(=O)(=O)n3ccc(/C=C/C(=O)NOC4CCCCO4)c3)cc2)cn1

HCID86621694

未命名化合物

收率 81.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

CONDITIONS

反应条件

温度: 90 °C

PROCEDURE

实验过程

(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (0.95 g) and [5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1.00 g) are dissolved under an inert gas atmosphere in dimethylethylenglycole (35 mL), and Pd(PPh3)3Cl2 (0.22 g) and a sodium carbonate solution (2.21 g dissolved in 21 water) is added and it is heated for 0.5 h at 90° C. After cooling the mixture is diluted with water, extracted with chloroform, and the combined organic phases are dried and evaporated. The residue is purified by silica gel flash chromatography CHCl3/THF (4:1). 0.97 g of the title compound are obtained with a melting point of 140-146° C.

WORKUP

后处理

temperatureAfter cooling the mixture
extractionextracted with chloroform
customthe combined organic phases are dried
customevaporated
customThe residue is purified by silica gel flash chromatography CHCl3/THF (4:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-fbda8e28a8d44d81bed3c85554a071de
来源数据集: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08815855B2
来源说明: uspto-grants-2014_08

反应 SMILES

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:28]([O:32][C:33](=[O:50])[NH:34][C:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][N:36]=1)([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:28]([O:32][C:33](=[O:50])[NH:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]3[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](=[O:19])[NH:20][O:21][CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][O:23]4)=[CH:12]3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:37][N:36]=1)([CH3:31])([CH3:29])[CH3:30]