HRID1272714

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID516892

Sodium Bicarbonate

CHNaO3

结构：CC1(C)OB(c2ccc(C(=O)NCC3CC3)cc2)OC1(C)C

HCID11483451

未命名化合物

结构：Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)c2ccc(C)c(Br)c2)cc1

HCID11750662

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)c2ccc(C)c(-c3ccc(C(=O)NCC4CC4)cc3)c2)cc1

HCID10301643

未命名化合物

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HCID3776

Isopropanol

C3H8O

CONDITIONS

反应条件

温度: 85 °C

PROCEDURE

实验过程

3-Bromo-N-[3-t-butyl-1-(4-methylphenyl)-pyrazol-5-yl]-4-methylbenzamide (Intermediate 2 2, 43 mg), N-cyclopropylmethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (33 mg), tetrakis(triphenylphosphine)palladium (2 mg) and aqueous sodiumhydrogen carbonate (1M, 0;5 ml) were mixed in propan-2-ol (2 ml) and heated at 85° C. under nitrogen for 96 hrs. The cooled reaction was absorbed onto silica and applied to a SPE cartridge (Si, 5 g) and eluted with an ethyl acetate/cylohexane gradient (0–100% ethyl acetate). The product fractions were reduced to dryness under vacuum to give N3-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-N4′-(cyclopropylmethyl)-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide.

WORKUP

后处理

customThe cooled reaction
customwas absorbed onto silica
washeluted with an ethyl acetate/cylohexane gradient (0–100% ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-20fb620360b249b58085c8d7819b7bb6
来源数据集: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07208629B2
来源说明: uspto-grants-2007_04

反应 SMILES

Br[C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:5]([NH:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=[C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:9]=1)=[O:6].[CH:28]1([CH2:31][NH:32][C:33](=[O:49])[C:34]2[CH:39]=[CH:38][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:36][CH:35]=2)[CH2:30][CH2:29]1.C(=O)([O-])O.[Na+]>CC(O)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>[C:20]([C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:37]3[CH:38]=[CH:39][C:34]([C:33]([NH:32][CH2:31][CH:28]4[CH2:30][CH2:29]4)=[O:49])=[CH:35][CH:36]=3)[C:26]([CH3:27])=[CH:25][CH:24]=2)=[O:6])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=1)([CH3:23])([CH3:22])[CH3:21]