HRID872323

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID21115800

未命名化合物

结构：CC(C)(C)OC(=O)NC1(c2ccc(-c3nc4ccc(Br)cn4c3-c3ccccc3)cc2)CCC1

HCID66665495

未命名化合物

PRODUCTS

生成物

结构：C=Cc1ccc2nc(-c3ccc(C4(NC(=O)OC(C)(C)C)CCC4)cc3)c(-c3ccccc3)n2c1

HCID66665743

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID6285

Tetraethylammonium bromide

C8H20BrN

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 120 °C

PROCEDURE

实验过程

A mixture of {1-[4-(6-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (70 mg, 60% purity by UPLC-MS), potassium carbonate (11.2 mg), tetraethylammonium bromide (22.1 mg), tributylvinyl stannane (38.5 mg) and trans-dichlorobis(triphenylphosphine) palladium (II) (1.7 mg) in THF (0.66 mL) under argon was heated at 120° C. for 45 min. On cooling the reaction was partitioned between DCM and water, the organic extract dried and concentrated to give the crude title compound which was used without further purification.

WORKUP

后处理

temperatureOn cooling the reaction
customwas partitioned between DCM and water
extractionthe organic extract
customdried
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d2c280c6d2174654aa5897fb9bdb1fd9
来源数据集: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08975265B2
来源说明: uspto-grants-2015_03

反应 SMILES

[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23](Br)=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:41](C([SnH3])=C(CCCC)CCCC)[CH2:42]CC>[Br-].C([N+](CC)(CC)CC)C.C1COCC1>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH:41]=[CH2:42])=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]