HRID906450

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID11780954

未命名化合物

结构：CC(C)(C)OC(=O)N1CCN(S(=O)(=O)c2c[nH]c(=O)c3ccc(Br)cc23)C[C@@H]1CO

HCID67392085

未命名化合物

PRODUCTS

生成物

HCID21882781

未命名化合物

收率 10%

结构：CC(C)(CO[Si](C)(C)C(C)(C)C)Cn1cc(S(=O)(=O)N2CCN(C(=O)OC(C)(C)C)[C@@H](CO)C2)c2cc(Br)ccc2c1=O

HCID67391011

未命名化合物

收率 97%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 110 °C

PROCEDURE

实验过程

A solution of tert-butyl (2R)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]-2-(hydroxymethyl)piperazine-1-carboxylate (Example 49a, 0.855 g) dissolved in DMF (20 mL) was treated with (3-bromo-2,2-dimethylpropoxy)(tert-butyl)dimethylsilane (0.718 g) and cesium carbonate (1.109 g). The reaction was heated at 110° C. for 107 h. The reaction was cooled and partitioned between ethyl acetate and brine. The organics were washed with brine (×3), dried (MgSO4), filtered and evaporated to leave the crude product. This was purified (SiO2 chromatography, elution with 100% DCM then 10-50% ethyl acetate/isohexane) to afford the subtitle compound (0.580 g).

WORKUP

后处理

temperatureThe reaction was cooled
custompartitioned between ethyl acetate and brine
washThe organics were washed with brine (×3)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customto leave the crude product
customThis was purified (
washSiO2 chromatography, elution with 100% DCM

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c356dc1fed5747c5b78a0bd08fc5a88a
来源数据集: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08012980B2
来源说明: uspto-grants-2011_09

反应 SMILES

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@@H:18]([CH2:29][OH:30])[CH2:17]1)(=[O:15])=[O:14].Br[CH2:32][C:33]([CH3:44])([CH3:43])[CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:22]([O:24][CH2:25][CH3:28])(=[O:23])[CH3:32].[CH3:11][CH2:2][CH2:3][CH:4]([CH3:9])[CH3:5].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:32][C:33]([CH3:44])([CH3:43])[CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH:6]=[C:5]2[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C@@H:18]([CH2:29][OH:30])[CH2:17]1)(=[O:15])=[O:14]