HRID906451

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

结构：Cc1c(F)cc(C(=O)NC2CC2)cc1B1OC(C)(C)C(C)(C)O1

HCID21914563

未命名化合物

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

PRODUCTS

生成物

结构：Cc1c(F)cc(C(=O)NC2CC2)cc1-c1ccc2c(=O)n(CC(C)(C)CO[Si](C)(C)C(C)(C)C)cc(S(=O)(=O)N3CCN(C(=O)OC(C)(C)C)[C@@H](CO)C3)c2c1

HCID86640972

未命名化合物

收率 80%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 75 °C

PROCEDURE

实验过程

A solution of tert-butyl (2R)-4-{[6-bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-4-yl]sulfonyl}-2-(hydroxymethyl)piperazine-1-carboxylate (Example 49b, 0.58 g) in DMF (10 mL) was treated with N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.263 g), Pd-118 (0.016 g) and potassium carbonate (0.228 g). The resulting mixture was stirred at 75° C. for 6 h. The cooled reaction was concentrated under reduced pressure then purified (SiO2 chromatography, loaded in DCM, flushed with isohexane (100 mL), then DCM (200 mL), followed by a 10-100% gradient of ethyl acetate/isohexane) to afford the subtitle compound (0.537 g).

WORKUP

后处理

customThe cooled reaction
concentrationwas concentrated under reduced pressure
customthen purified (SiO2 chromatography
customflushed with isohexane (100 mL)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-17c2cef926e54ea0a9e828edfc9f373e
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[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:25])([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:6]=[C:5]2[S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@@H:31]([CH2:42][OH:43])[CH2:30]1)(=[O:28])=[O:27].[CH:44]1([NH:47][C:48](=[O:66])[C:49]2[CH:54]=[C:53](B3OC(C)(C)C(C)(C)O3)[C:52]([CH3:64])=[C:51]([F:65])[CH:50]=2)[CH2:46][CH2:45]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Si:17]([O:16][CH2:15][C:14]([CH3:24])([CH3:25])[CH2:13][N:7]1[CH:6]=[C:5]([S:26]([N:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[C@@H:31]([CH2:42][OH:43])[CH2:30]2)(=[O:28])=[O:27])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:53]3[CH:54]=[C:49]([C:48](=[O:66])[NH:47][CH:44]4[CH2:45][CH2:46]4)[CH:50]=[C:51]([F:65])[C:52]=3[CH3:64])[CH:3]=2)[C:8]1=[O:12])([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:19])[CH3:18]