HRID595762

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID12259383

2,6-Dichloropyridine-3-carbaldehyde

C6H3Cl2NO

结构：CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(C)S(C)(=O)=O)c(B3OC(C)(C)C(C)(C)O3)cc12

HCID68239402

未命名化合物

PRODUCTS

生成物

结构：CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(C)S(C)(=O)=O)c(-c3ccc(C=O)c(Cl)n3)cc12

HCID90332470

未命名化合物

收率 86.3%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cl[Pd]Cl.[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1

催化剂HCID178418228

Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)

C34H28Cl2FeP2Pd

溶剂HCID962

Water

H2O

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

To a degassed solution of 2,6-dichloronicotinaldehyde (315 mg, 1.79 mmol) and 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (600 mg, 1.19 mmol) in 1,4-dioxane (8 mL) and water (300 μL) was added K2CO3 (330 mg, 2.40 mmol) and Pd(dppf)Cl2 (175 mg, 0.24 mmol) under N2 protection. The resulting mixture was heated to 80° C. and stirred at this temperature overnight. The reaction was cooled, filtered through a pad of celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-30% EtOAc/DCM) to provide 5-(6-chloro-5-formylpyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (530 mg, yield: 86%) MS (M+H)+: 516.

WORKUP

后处理

temperatureThe reaction was cooled
filtrationfiltered through a pad of celite
washwashed with ethyl acetate
customThe combined filtrate was evaporated in vacuo
customThe resulting residue was purified
washcolumn chromatography (eluted with 0-30% EtOAc/DCM)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-16b807a693854fa8a20c44a7a8574b44
来源数据集: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09243002B2
来源说明: uspto-grants-2016_01

反应 SMILES

[Cl:1][C:2]1[N:9]=[C:8](Cl)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[CH:30]=[C:29]([N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33])[C:28](B4OC(C)(C)C(C)(C)O4)=[CH:27][C:21]=3[C:22]=2[C:23]([NH:25][CH3:26])=[O:24])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[N:9]=[C:8]([C:28]2[C:29]([N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][C:20]3[O:19][C:18]([C:15]4[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=4)=[C:22]([C:23]([NH:25][CH3:26])=[O:24])[C:21]=3[CH:27]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]