HRID531613

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)N(c1cc(-c2cnc3c(c2)c(I)cn3C(=O)OC(C)(C)C)ccc1F)S(C)(=O)=O

HCID90064828

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)c2ncc(-c3ccc(F)c(N(C(=O)OC(C)(C)C)S(C)(=O)=O)c3)cc12

HCID131735670

未命名化合物

收率 91.5%

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-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-fluorophenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (Intermediate 66A)(85 mg, 0.134 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) (93 mg, 0.269 mmol) using sodium carbonate (43 mg, 0.404 mmol) and Pd(PPh3)2Cl2 (5 mg, 0.006) in DME/water (20/4 mL) to afford 89 mg of the crude compound. MS: m/z=670.2 (M+1) (de boc mass observed).

WORKUP

后处理

customreaction conditions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-471acb07715b4fe19d6bda27c10c7596
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]([C:13]1[CH:14]=[C:15]([C:20]2[CH:21]=[C:22]3[C:28](I)=[CH:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23]3=[N:24][CH:25]=2)[CH:16]=[CH:17][C:18]=1[F:19])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:37][C:38]1[CH:39]=[C:40]([CH:58]=[C:59]([F:61])[CH:60]=1)[CH2:41][N:42]1[C:46]([CH3:47])=[C:45](B2OC(C)(C)C(C)(C)O2)[C:44]([CH3:57])=[N:43]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:20]2[CH:21]=[C:22]3[C:28]([C:45]4[C:44]([CH3:57])=[N:43][N:42]([CH2:41][C:40]5[CH:58]=[C:59]([F:61])[CH:60]=[C:38]([F:37])[CH:39]=5)[C:46]=4[CH3:47])=[CH:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23]3=[N:24][CH:25]=2)[CH:16]=[CH:17][C:18]=1[F:19])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]