HRID238066

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID31275

1,4-Dioxane

C4H8O2

结构：CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nc2ccccc2s1

HCID3762392

2-(Tributylstannyl)-1,3-benzothiazole

C19H31NSSn

$结构：CCOC(=O)[C@@]12C[C@@H]1/C=C\CCCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@H](Oc3nc4ccccc4nc3Cl)C[C@H]1C(=O)N2$

HCID25010469

未命名化合物

PRODUCTS

生成物

$结构：CCOC(=O)[C@@]12C[C@@H]1/C=C\CCCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@H](Oc3nc4ccccc4nc3-c3ccccc3)C[C@H]1C(=O)N2$

HCID68500607

未命名化合物

收率 92.7%

AUXILIARIES

试剂、催化剂与溶剂

结构：[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1

催化剂HCID11979704

未命名化合物

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

To a microwave vessel was added the product from 1b (700 mg. 1.07 mmole), 2-(tributylstannyl)benzo[d]thiazole (905 mg., 2.13 mmole), palladium-tetrakis(triphenylphosphine) (113 mg., 0.11 mmole) and dioxane (5 ml.). The vessel was evacuated and nitrogen introduced, which was repeated twice. The mixture was reacted in a microwave reactor at 110 degrees C. for 1 hr. The reaction was diluted with MeCN and washed 3 times with hexane. The MeCN layer was evaporated and purified by column chromatography on silica gel (CHCl3-EtOAc gradient) to obtain the title compound (692 mg., 86% yield). MS (ESI): m/z=755.2 [M+H].

WORKUP

后处理

customThe vessel was evacuated
additionnitrogen introduced
customThe mixture was reacted in a microwave reactor at 110 degrees C
washwashed 3 times with hexane
customThe MeCN layer was evaporated
custompurified by column chromatography on silica gel (CHCl3-EtOAc gradient)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ed3ea373c4d54cef8e2c09df5578ea0f
来源数据集: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08642538B2
来源说明: uspto-grants-2014_02

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[C:38](Cl)=[N:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH2:27][C@H:21]2[C:20](=[O:40])[NH:19][C@:18]2([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:41][C@@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)C1S[C:54]2[CH:60]=[CH:59][CH:58]=[CH:57][C:55]=2N=1)CCC.O1CCOCC1>CC#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[C:38]([C:54]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:55]=4)=[N:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH2:27][C@H:21]2[C:20](=[O:40])[NH:19][C@:18]2([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:41][C@@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]