HRID79183

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21

HCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

HCID23676156

Sodium t-butoxide

C4H9NaO

HCID58299585

未命名化合物

结构：CC(C)(C)[Si](C)(C)OCCN1CCN(c2ccc(Cl)nc2)CC1

HCID58299745

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)[Si](C)(C)OCCN1CCN(c2ccc(Nc3ncc4c5ccncc5n(C5CCCC5)c4n3)nc2)CC1

HCID58299849

未命名化合物

收率 25%

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 120 °C

PROCEDURE

实验过程

A 10 mL reaction vessel was charged with compound 4 (153 mg, 604 μmol), compound 247 (215 mg, 604 μmol), tris(dibenzylideneacetone)-dipalladium (0) (41.5 mg, 45.3 μmol), sodium t-butoxide (69.7 mg, 725 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (52.4 mg, 90.6 μmol), and dioxane (3 mL). The reaction was purged with argon and heated with microwave energy at 120° C. for 3.5 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA, then ethyl acetate+2.5% TEA/0-5% methanol) afforded compound 296 as a yellow solid (85 mg, 25%).

WORKUP

后处理

customA 10 mL reaction vessel
customThe reaction was purged with argon
customThe solvent was removed in vacuo and silica gel chromatography (
washgradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-aacf3e6ba81b4af39bfd11a0938c3381
来源数据集: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08841312B2
来源说明: uspto-grants-2014_09

反应 SMILES

[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH2:15])[N:13]=[CH:14][C:9]=3[C:8]3[CH:16]=[CH:17][N:18]=[CH:19][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:21]1[N:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Si:36]([O:35][CH2:34][CH2:33][N:30]1[CH2:31][CH2:32][N:27]([C:24]2[CH:23]=[CH:22][C:21]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[C:8]5[CH:16]=[CH:17][N:18]=[CH:19][C:7]=5[N:6]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)[C:10]=4[N:11]=3)=[N:26][CH:25]=2)[CH2:28][CH2:29]1)([C:39]([CH3:42])([CH3:40])[CH3:41])([CH3:37])[CH3:38]