HRID366710

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15550485

未命名化合物

$结构：COc1cc[nH]c1/C=C1\C(=O)Nc2ccc([N+](=O)[O-])c(Br)c21$

HCID18359293

未命名化合物

2 次

PRODUCTS

生成物

$结构：COc1cc[nH]c1/C=C1\C(=O)Nc2ccc([N+](=O)[O-])c(C#CC3(O)CCOCC3)c21$

HCID18366111

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

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HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8471

Triethylamine

C6H15N

PROCEDURE

实验过程

Using Method C above, 4-ethynyl-tetrahydro-pyran-4-ol (43.3 mg, 0.34 mmol) (Example 85A) was coupled with (Z)-1,3-dihydro-4-bromo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (50 mg, 0.14 mmol) (Starting Material 7) using (Ph3P)4Pd (16 mg) and Cul (3.0 mg) as catalyst in DMF (4 mL) and Et3N (4 mL) as solvent at 85° C. for 18 h to give (Z)-1,3-Dihydro-4-[(4-hydroxy-tetrahydro-pyran-4-yl)ethynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one. (Yield 30 mg, 53%).

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-72190af0a1a14d0489624534b1410206
来源数据集: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06130239
来源说明: uspto-grants-2000_10

反应 SMILES

[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[CH:2].Br[C:11]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]2[C:12]=1/[C:13](=[CH:24]/[C:25]1[NH:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31])/[C:14](=[O:23])[NH:15]2>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.CN(C=O)C.CCN(CC)CC>[OH:9][C:3]1([C:1]#[C:2][C:11]2[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]3[C:12]=2/[C:13](=[CH:24]/[C:25]2[NH:26][CH:27]=[CH:28][C:29]=2[O:30][CH3:31])/[C:14](=[O:23])[NH:15]3)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1