HRID1751416

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID11430

Potassium Carbonate

CK2O3

结构：CC(C)(C)OC(=O)N1CC(C#N)CC1c1ncc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)[nH]1

HCID66620822

未命名化合物

结构：C=C1CC(c2ncc(-c3ccc4cc(Br)ccc4c3)[nH]2)N(C(=O)C(NC(=O)OC)C(C)C)C1

HCID69675294

未命名化合物

PRODUCTS

生成物

结构：C=C1CC(c2ncc(-c3ccc4cc(-c5ccc(-c6cnc(C7CC(C#N)CN7C(=O)OC(C)(C)C)[nH]6)cc5)ccc4c3)[nH]2)N(C(=O)C(NC(=O)OC)C(C)C)C1

HCID77335387

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8071

未命名化合物

PROCEDURE

实验过程

(1-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-4-methylene-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (202 mg, 0.392 mmol), 4-Cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (181 mg, 0.392 mmol), Pd[PPh3] (45.6 mg, 0.0392 mmol), potassium carbonate (108 mg, 0.784 mmol) were heated in DME (3 mL)/water (0.4 mL) at 120° C. for 20 minutes under microwave conditions. The volatiles were removed in vacuo and the crude was partitioned between EtOAc and brine/aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate. Filtration and evaporation of solvents yielded the crude material, which was purified via flash chromatography on silica gel to yield the product. (161 mg).

WORKUP

后处理

customThe volatiles were removed in vacuo
customthe crude was partitioned between EtOAc and brine/aqueous sodium bicarbonate solution
dry with materialThe organic layer was dried over sodium sulfate
filtrationFiltration and evaporation of solvents

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6a0395ea03564904a018d51ce01dd5bc
来源数据集: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09156823B2
来源说明: uspto-grants-2015_10

反应 SMILES

[CH3:1][O:2][C:3](=[O:33])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][C:14](=[CH2:16])[CH2:13][CH:12]1[C:17]1[NH:18][C:19]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27](Br)[CH:28]=3)[CH:23]=2)=[CH:20][N:21]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[C:34]([O:38][C:39]([N:41]1[CH2:45][CH:44]([C:46]#[N:47])[CH2:43][CH:42]1[C:48]1[NH:49][C:50]([C:53]2[CH:58]=[CH:57][C:56](B3OC(C)(C)C(C)(C)O3)=[CH:55][CH:54]=2)=[CH:51][N:52]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+].O>COCCOC>[C:34]([O:38][C:39]([N:41]1[CH2:45][CH:44]([C:46]#[N:47])[CH2:43][CH:42]1[C:48]1[NH:49][C:50]([C:53]2[CH:58]=[CH:57][C:56]([C:27]3[CH:26]=[CH:25][C:24]4[C:29](=[CH:30][CH:31]=[C:22]([C:19]5[NH:18][C:17]([CH:12]6[CH2:13][C:14](=[CH2:16])[CH2:15][N:11]6[C:9](=[O:10])[CH:5]([NH:4][C:3]([O:2][CH3:1])=[O:33])[CH:6]([CH3:8])[CH3:7])=[N:21][CH:20]=5)[CH:23]=4)[CH:28]=3)=[CH:55][CH:54]=2)=[CH:51][N:52]=1)=[O:40])([CH3:37])([CH3:35])[CH3:36]