HRID879368

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCOC(=O)[C@@H](OC(C)(C)C)c1c(C)cc2nc(-c3ccnc(Cl)c3)sc2c1-c1ccc(Cl)cc1

HCID86700142

未命名化合物

结构：CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc2c(=O)n(C)n(C)c2c1

HCID86700175

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)[C@@H](OC(C)(C)C)c1c(C)cc2nc(-c3ccnc(-c4ccc5c(=O)n(C)n(C)c5c4)c3)sc2c1-c1ccc(Cl)cc1

HCID86700174

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

结构：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HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 100 °C

PROCEDURE

实验过程

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (32.0 mg, 0.061 mmol) and 1,2-dimethyl-6-(tributylstannyl)-1H-indazol-3(2H)-one (33.0 mg, 0.073 mmol) in dioxane (0.8 mL) was added Pd(PPh3)4 (4.0 mg, 0.003 mmol) and CuI (4.0 mg, 0.018 mmol). The reaction was degassed for 5 minutes with N2 and then heated at 100° C. for 2 days. Concentrated in vacuo and then purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C36H36ClN4O4S: 655.2; found: 655.3.

WORKUP

后处理

customThe reaction was degassed for 5 minutes with N2
concentrationConcentrated in vacuo
custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4182ffa4d87a4d5b8a2412a19d03002e
来源数据集: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08987250B2
来源说明: uspto-grants-2015_03

反应 SMILES

[C:1]([O:5][C@@H:6]([C:12]1[C:27]([CH3:28])=[CH:26][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21](Cl)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37]1[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([Sn](CCCC)(CCCC)CCCC)[CH:44]=2)[C:39](=[O:59])[N:38]1[CH3:60]>O1CCOCC1.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.[Cu]I>[C:1]([O:5][C@@H:6]([C:12]1[C:27]([CH3:28])=[CH:26][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:43]4[CH:44]=[C:45]5[C:40]([C:39](=[O:59])[N:38]([CH3:60])[N:37]5[CH3:36])=[CH:41][CH:42]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]