HRID1913385

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8083

Morpholine

C4H9NO

结构：c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1

HCID634876

2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

C44H32P2

HCID23676156

Sodium t-butoxide

C4H9NaO

结构：CCOC(=O)c1cc(-c2ccc(Br)cc2)n(-c2cccc(S(C)(=O)=O)c2)c1C

HCID24895704

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)c1cc(-c2ccc(N3CCOCC3)cc2)n(-c2cccc(S(C)(=O)=O)c2)c1C

HCID24895710

未命名化合物

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HCID1140

Toluene

C7H8

PROCEDURE

实验过程

A mixture of Example 2 (0.05 g, 0.108 mmol), morpholine (0.023 g, 0.24 mmol), Pd2(dba)3 (0.002 g), BINAP (0.0035 g) and sodium tert-butoxide (0.017 g) in 5 mL of toluene heated to 90° C. and stirred for 18 hours. After cooling, the mixture was filtered through diatomaceous earth, concentrated under reduced pressure and purified by flash chromatography using a gradient of ethyl acetate (0-50%) in DCM to provide the titled compound. 1H NMR (CDCl3) δ ppm 1.31 (3H), 2.20 (3H), 2.80 (3H), 3.1 (4H), 3.70 (4H), 4.25 (2H), 6.71 (2H), 6.80 (1H), 7.30-7.90 (6H); MS (ESI) m/z 469 (M+H).

WORKUP

后处理

temperatureAfter cooling
filtrationthe mixture was filtered through diatomaceous earth
concentrationconcentrated under reduced pressure
custompurified by flash chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-336d6b57e01c4ffea22c755ed3c221f2
来源数据集: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08609713B2
来源说明: uspto-grants-2013_12

反应 SMILES

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)[C:11]([CH3:23])=[C:10]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:9]=2)=[CH:4][CH:3]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)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]>[CH2:27]([O:26][C:24]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:3][CH:4]=2)[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=2)[C:11]=1[CH3:23])=[O:25])[CH3:28]