HRID531574

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：Cc1nn(Cc2cc(F)cc(F)c2)c(C)c1B1OC(C)(C)C(C)(C)O1

HCID90031220

未命名化合物

2 次

结构：CC(C)(C)OC(=O)N1CCN(c2ccc(-c3cc4c(I)cn(C(=O)OC(C)(C)C)c4nc3C3CC3)cc2)CC1

HCID90064816

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1nn(Cc2cc(F)cc(F)c2)c(C)c1-c1cn(C(=O)OC(C)(C)C)c2nc(C3CC3)c(-c3ccc(N4CCN(C(=O)OC(C)(C)C)CC4)cc3)cc12

HCID90030898

未命名化合物

收率 45.1%

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HCID18180031

未命名化合物

PROCEDURE

实验过程

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-6-cyclopropyl-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate 57) (120 mg, 0.186 mmol) was coupled with 1-(3,5-difluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 24) (97.24 mg, 0.27 mmol) in sodium carbonate (59.1 mg, 0.483 mmol), Pd(PPh3)2Cl2 (6.5 mg, 0.009 mmol), 1,2-dimethoxyethane/water (15/2 ml) to afford 62 mg (45% yield) of titled compound. MS: m/z=739.2 (M+1).

WORKUP

后处理

customreaction conditions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-73bdea813c4d48b48b24185f1655951d
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09353107B2
来源说明: uspto-grants-2016_05

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:31](I)=[CH:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:23]4=[N:24][C:25]=3[CH:26]3[CH2:28][CH2:27]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:40][C:41]1[CH:42]=[C:43]([CH:61]=[C:62]([F:64])[CH:63]=1)[CH2:44][N:45]1[C:49]([CH3:50])=[C:48](B2OC(C)(C)C(C)(C)O2)[C:47]([CH3:60])=[N:46]1.C(=O)([O-])[O-].[Na+].[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.COCCOC.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:31]([C:48]5[C:47]([CH3:60])=[N:46][N:45]([CH2:44][C:43]6[CH:61]=[C:62]([F:64])[CH:63]=[C:41]([F:40])[CH:42]=6)[C:49]=5[CH3:50])=[CH:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:23]4=[N:24][C:25]=3[CH:26]3[CH2:28][CH2:27]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]