HRID589195

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC

HCID619414

Tributyl(1-ethoxyvinyl)stannane

C16H34OSn

结构：CC(C)(C)OC(=O)N1C2CCC1CN(c1nc3c(-c4ccc(-c5ccccc5)nc4)cnn3c(N(COCC[Si](C)(C)C)COCC[Si](C)(C)C)c1Br)C2

HCID67294397

未命名化合物

PRODUCTS

生成物

结构：C=C(OCC)c1c(N2CC3CCC(C2)N3C(=O)OC(C)(C)C)nc2c(-c3ccc(-c4ccccc4)nc3)cnn2c1N(COCC[Si](C)(C)C)COCC[Si](C)(C)C

HCID67295001

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HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 100 °C

PROCEDURE

实验过程

A degassed mixture of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (256 mg, 0.31 mmol), Pd(PPh3)4 (35 mg, 0.031 mmol), tributyl(1-ethoxyvinyl)stannane (221 mg, 0.61 mmol) in dioxane (6 mL) was heated at 100° C. overnight. The reaction mixture was cooled to room temperature, filtered through a 9:1 SiO2:KF plug and concentrated in vacuo. Purification by column chromatography afforded tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate, LCMS tR=3.58 Min (10 min run, UV254nm). Mass calculated for M+H 828.45, observed LC/MS m/z 828.07 (M+H).

WORKUP

后处理

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a 9:1 SiO2
concentrationKF plug and concentrated in vacuo
customPurification by column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-60b8b55ae5cb43bb89eab344a924edff
来源数据集: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09227971B2
来源说明: uspto-grants-2016_01

反应 SMILES

[CH3:1][Si:2]([CH3:54])([CH3:53])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[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]([N:29]2[CH2:35][CH:34]3[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:31]([CH2:32][CH2:33]3)[CH2:30]2)[C:9]=1Br.C([Sn](CCCC)(CCCC)[C:60]([O:62][CH2:63][CH3:64])=[CH2:61])CCC>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]([CH3:54])([CH3:53])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[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]([N:29]2[CH2:35][CH:34]3[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:31]([CH2:32][CH2:33]3)[CH2:30]2)[C:9]=1[C:60]([O:62][CH2:63][CH3:64])=[CH2:61]