HRID531596

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

反应SMILES：CC1(C)OB(c2cnn(Cc3cccnc3)c2)OC1(C)C

HCID17999185

3-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}pyridine

C15H20BN3O2

2 次

反应SMILES：COc1ncc(-c2cnc3c(c2)c(I)cn3C(=O)OC(C)(C)C)cc1N(C(=O)OC(C)(C)C)S(C)(=O)=O

HCID90064817

未命名化合物

2 次

PRODUCTS

产物

反应SMILES：COc1ccc(-c2cnc3c(c2)c(-c2cnn(Cc4cccnc4)c2)cn3C(=O)OC(C)(C)C)cc1N(C(=O)OC(C)(C)C)S(C)(=O)=O

HCID131735669

未命名化合物

收率 38.2%

AUXILIARIES

试剂、催化剂与溶剂

反应SMILES：Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1

催化剂HCID178418476

未命名化合物

溶剂HCID86587398

未命名化合物

PROCEDURE

实验过程

Using similar reaction conditions as described in step-i of example-1, tert-butyl 5-(5-(N-(tert-butoxycarbonyl)methylsulfonamido)-6-methoxypyridin-3-yl)-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate 66P) (150 mg, 0.233 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (intermediate 64) (73 mg, 0.256 mmol) using Pd(PPh3)2Cl2 (9 mg, 0.0116 mol) and sodium carbonate (74 mg, 0.699 mmol) in toluene/ethanol/water (3/3/2 ml) to afford 60 mg (38% yield) of the titled compound after purification by column (Silica gel 60/120) using 30% ethyl acetate in hexane as eluent. MS: m/z=675.1 (M+1).

WORKUP

后处理

customreaction conditions

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-761a3e6ea3804a69b0df4462de6a5a00
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US09353107B2
来源说明: uspto-grants-2016_05

反应SMILES

[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]3[C:29](I)=[CH:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]3=[N:25][CH:26]=2)[CH:16]=N[C:18]=1[O:19][CH3:20])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:46]2[CH:47]=[N:48][N:49]([CH2:51][C:52]3[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=3)[CH:50]=2)O1.[C:59](=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.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>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]3[C:29]([C:46]4[CH:47]=[N:48][N:49]([CH2:51][C:52]5[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=5)[CH:50]=4)=[CH:28][N:27]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:24]3=[N:25][CH:26]=2)[CH:16]=[CH:59][C:18]=1[O:19][CH3:20])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:2])([CH3:4])[CH3:3]