HRID1392714

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

反应SMILES：CCOC(=O)[C@@H]1C[C@H]1c1ccc(Br)cc1

HCID66578655

未命名化合物

反应SMILES：CSCCNC(=O)c1cn(-c2cccc(Br)c2)c2ncccc2c1=O

HCID69160385

未命名化合物

PRODUCTS

产物

反应SMILES：CCOC(=O)C1CC1c1ccc(-c2cccc(-n3cc(C(=O)NCCSC)c(=O)c4cccnc43)c2)cc1

HCID69313869

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

反应SMILES：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID1031

1-Propanol

C3H8O

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

A mixture of amide from step 1 (1 eq), ethyl 2-(trans)-(4-bromophenyl)cyclopropanecarboxylate from EXAMPLE 1, step 1 (1 eq), Na2CO3 (3.5eq.; 2M in H2O), Pd(PPh3)4 (0.05 eq) in n-propanol (0.1M) was stirred at 80° C. for 3 h. The mixture was cooled to rt, quenched with brine and diluted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was triturated in ether/MeOH, isolated by filtration and washed with ether to afford the title compound as a solid.

WORKUP

后处理

temperatureThe mixture was cooled to rt
customquenched with brine
additiondiluted with EtOAc
washThe organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was triturated in ether/MeOH
customisolated by filtration
washwashed with ether

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-953a890e4ea64df3ac1b48d81302a5ff
来源数据集: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US07342024B2
来源说明: uspto-grants-2008_03

反应SMILES

Br[C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([NH:21][CH2:22][CH2:23][S:24][CH3:25])=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([C@@H:33]2[CH2:35][C@H:34]2[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][S:24][CH2:23][CH2:22][NH:21][C:19]([C:10]1[C:11](=[O:18])[C:12]2[C:17](=[N:16][CH:15]=[CH:14][CH:13]=2)[N:8]([C:4]2[CH:3]=[C:2]([C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:35][CH:34]4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:28]=3)[CH:7]=[CH:6][CH:5]=2)[CH:9]=1)=[O:20]