HRID2246635

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6344

Dichloromethane

CH2Cl2

HCID516892

Sodium Bicarbonate

CHNaO3

结构：CC(C)(C)OC(=O)N1CCN(c2n[nH]c3cc(Br)ccc23)CC1

HCID58899616

未命名化合物

2 次

结构：CCNC(=O)c1ccc(C)c(B2OC(C)(C)C(C)(C)O2)c1

HCID60133236

未命名化合物

2 次

PRODUCTS

生成物

结构：CCNC(=O)c1ccc(C)c(-c2ccc3c(N4CCN(C(=O)OC(C)(C)C)CC4)n[nH]c3c2)c1

HCID58899609

未命名化合物

收率 82.2%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID962

Water

H2O

溶剂HCID3776

Isopropanol

C3H8O

PROCEDURE

实验过程

A mixture, of 1,1-dimethylethyl 4-(6-bromo-1H-indazol-3-yl)-1-piperazinecarboxylate (Intermediate 6, 660 mg) N-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 10, 598 mg) tetrakis(triphenylphosphine)palladium (25 mg) and aqueous sodium hydrogen carbonate (1M, 1.5 ml) in isopropanol (6 ml) was stirred at 150° C. for 20 min in a microwave oven. DCM and water were added and the organic phase was separated using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by chromatography on a silica column eluting with a cyclohexane/ethyl acetate gradient to give the title compound (660 mg).

WORKUP

后处理

customthe organic phase was separated
concentrationconcentrated under vacuum
customThe residue was purified by chromatography on a silica column
washeluting with a cyclohexane/ethyl acetate gradient

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c595b4cefe2e4419bf98c5a9c9295a3e
来源数据集: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07687532B2
来源说明: uspto-grants-2010_03

反应 SMILES

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:24]([NH:26][C:27](=[O:44])[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=1)[CH3:25].C(=O)([O-])O.[Na+].C(Cl)Cl>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:24]([NH:26][C:27]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([N:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:29]=1)=[O:44])[CH3:25]