HRID1913271

反应详情

EQUATION

反应方程式

REACTANTS

反应物

反应SMILES：CCOC(=O)C1(C)CC=C(c2nc3c(-c4ccc(-c5ccccc5)nc4)cnn3c(N(COCC[Si](C)(C)C)COCC[Si](C)(C)C)c2Br)CC1

HCID68089466

未命名化合物

PRODUCTS

产物

$反应SMILES：CCO/C=C\c1c(C2=CCC(C)(C(=O)OCC)CC2)nc2c(-c3ccc(-c4ccccc4)nc3)cnn2c1N(COCC[Si](C)(C)C)COCC[Si](C)(C)C$

HCID68111075

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

反应SMILES：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

A mixture of ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate (Int-18g, 48 mg, 0.061 mmol), (Z)-1-ethoxy-2-(tributylstannyl)ethane (72 mg), Pd(PPh3)4 (11 mg, 0.01 mmol) in dioxane (3 ml) was stirred at 100° C. under Ar for 8 h. After cooling to rt, the reaction mixture was passed through a short SiO2/KF (9:1) plug to removed majority of the Sn species. The filtrate was concentrated to give (Z)-ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(2-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate (Int-18h) which was used in the next step directly without further purification. HPLC-MS tR=3.02 min (UV254 nm); mass calculated for formula C43H61N5O5Si2 783.4, observed LCMS m/z 784.2 (M+H).

WORKUP

后处理

temperatureAfter cooling to rt
customto removed majority of the Sn species
concentrationThe filtrate was concentrated

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-9d07c636b05f44f48b6ee41af8df9a77
来源数据集: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US08609675B2
来源说明: uspto-grants-2013_12

反应SMILES

[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([C:29]2[CH2:34][CH2:33][C:32]([CH3:40])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH:30]=2)[C:9]=1Br>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>[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([C:29]2[CH2:34][CH2:33][C:32]([CH3:40])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH:30]=2)[C:9]=1/[CH:32]=[CH:35]\[O:37][CH2:38][CH3:39]