HRID531667

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(Cc2cccc(F)c2)c(C)c1B1OC(C)(C)C(C)(C)O1

HCID90030671

1-[(3-Fluorophenyl)methyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

C18H24BFN2O2

2 次

结构：CC(C)(C)OC(=O)N1CCC(N(C(=O)OC(C)(C)C)c2ccc(-c3cnc4c(c3)c(I)cn4C(=O)OC(C)(C)C)cc2)CC1

HCID90031137

未命名化合物

2 次

PRODUCTS

生成物

结构：Cc1nn(Cc2cccc(F)c2)c(C)c1-c1cn(C(=O)OC(C)(C)C)c2ncc(-c3ccc(N(C(=O)OC(C)(C)C)C4CCN(C(=O)OC(C)(C)C)CC4)cc3)cc12

HCID118523919

未命名化合物

收率 25.3%

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-(4-((tert-butoxycarbonyl)(1-(tert-butoxycarbonyl)piperidin-4-yl)amino)phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate 66H) (150 mg, 0.20 mmol) was coupled with 1-(3-fluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 16) (89 mg, 0.27 mmol) using Pd(dppf)Cl2 (8 mg, 0.01 mmol) and sodium carbonate (63 mg, 0.6 mmol) in toluene/ethanol/water (20/10/5 ml) to afford 40 mg (25.3% yield) of the titled compound after column purification using 35% ethyl acetate in hexane as eluent. MS: m/z=694.9 (M-Boc+1).

WORKUP

后处理

customreaction conditions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1d81ed83ba7e4137b3b581001fe206ba
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]([CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]3[C:23](I)=[CH:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]3=[N:19][CH:20]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:45][C:46]1[CH:47]=[C:48]([CH:66]=[CH:67][CH:68]=1)[CH2:49][N:50]1[C:54]([CH3:55])=[C:53](B2OC(C)(C)C(C)(C)O2)[C:52]([CH3:65])=[N:51]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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]>[C:1]([O:5][C:6]([N:8]([CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]3[C:23]([C:53]4[C:52]([CH3:65])=[N:51][N:50]([CH2:49][C:48]5[CH:66]=[CH:67][CH:68]=[C:46]([F:45])[CH:47]=5)[C:54]=4[CH3:55])=[CH:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]3=[N:19][CH:20]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]