HRID2234066

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID11776

Triphenylphosphine

C18H15P

HCID23092463

未命名化合物

结构：Cc1c(B2OC(C)(C)C(C)(C)O2)n(C(=O)OC(C)(C)C)c2ccccc12

HCID67148908

1,1-Dimethylethyl 3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

C20H28BNO4

PRODUCTS

生成物

结构：COc1nnc(-c2ccncc2)cc1-c1c(C)c2ccccc2n1C(=O)OC(C)(C)C

HCID67148566

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

溶剂HCID962

Water

H2O

溶剂HCID8071

未命名化合物

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Argon is passed for 30 min through a suspension of 333 mg 4-iodo-3-methoxy-6-pyridin-4-yl-pyridazine, 380 mg 3-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester, 294 mg potassium carbonate, and 111.6 mg triphenylphosphine in 4.8 ml DME and 2.4 ml water. 24 mg palladium (II) acetate is added and the mixture stirred under reflux for 3 h. The product is isolated by extraction with ethyl acetate and purified by chromatography on silica gel yielding 52.1 mg 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-methyl-indole-1-carboxylic acid tert-butyl ester.

WORKUP

后处理

temperatureunder reflux for 3 h
custompurified by chromatography on silica gel yielding 52.1 mg 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-methyl-indole-1-carboxylic acid tert-butyl ester

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9789ef1c782b42ce89af64f6230ef92e
来源数据集: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07709466B2
来源说明: uspto-grants-2010_05

反应 SMILES

I[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[O:14][CH3:15].[C:16]([O:20][C:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH3:32])=[C:24]1B1OC(C)(C)C(C)(C)O1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:16]([O:20][C:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH3:32])=[C:24]1[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[O:14][CH3:15])=[O:22])([CH3:19])([CH3:18])[CH3:17]