HRID69185

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8071

未命名化合物

HCID11430

Potassium Carbonate

CK2O3

结构：CC(C)(C)OC(=O)N1CC(n2cc(B3OC(C)(C)C(C)(C)O3)cn2)C1

HCID54576812

tert-Butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate

C17H28BN3O4

HCID58147516

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CC(n2cc(-c3ccc4ncc(Cc5cc6cccnc6cc5F)n4n3)cn2)C1

HCID68633118

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1

催化剂HCID178418476

未命名化合物

溶剂HCID86584982

未命名化合物

CONDITIONS

反应条件

温度: 95 °C

PROCEDURE

实验过程

A flask was charged with 6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 173.1, 100 mg, 0.320 mmol), 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]-azetidine-1-carboxylic acid tert-butyl ester (Stage 146.3), 168 mg, 0.480 mmol), DME (2 mL), Pd(PPh3)2Cl2 (11 mg, 0.05 mmol) and 2 M K2CO3 (432 μL, 0.863 mmol). The RM was heated at 95° C. for 2 h. The cool RM was diluted with EtOAc/NaHCO3. The organic phase was separated and washed with brine (2×) then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep®: silica gel column, DCM/(DCM/MeOH 19:1)=100:0→0:100) to afford the title compound as a foam (tR 4.33 min (conditions 3), MH+=500.1).

WORKUP

后处理

customThe organic phase was separated
washwashed with brine (2×)
dry with materialthen dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (CombiFlash® Companion System®

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1324ea0a58dc41c08238689e578002a6
来源数据集: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08822468B2
来源说明: uspto-grants-2014_09

反应 SMILES

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[C:23]([O:27][C:28]([N:30]1[CH2:33][CH:32]([N:34]2[CH:38]=[C:37](B3OC(C)(C)C(C)(C)O3)[CH:36]=[N:35]2)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].COCCOC.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.C([O-])(O)=O.[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:23]([O:27][C:28]([N:30]1[CH2:33][CH:32]([N:34]2[CH:38]=[C:37]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([CH2:11][C:12]5[CH:13]=[C:14]6[C:19](=[CH:20][C:21]=5[F:22])[N:18]=[CH:17][CH:16]=[CH:15]6)=[CH:9][N:10]=4)[N:7]=3)[CH:36]=[N:35]2)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]