HRID627805

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CC(C)(C)OC(=O)N1CCC(S(=O)(=O)c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1

HCID67481388

未命名化合物

结构：O=C1c2c(Cl)cccc2CN1c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2ncc(Br)nc12

HCID86676508

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCC(S(=O)(=O)c2ccc(-c3cnc4c(n3)c(N3Cc5cccc(Cl)c5C3=O)cn4C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)CC1

HCID71143607

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HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 110 °C

PROCEDURE

实验过程

2-(2-bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)-7-chloro-isoindolin-1-one (150 mg, 0.2476 mmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonylpiperidine-1-carboxylate (112 mg, 0.2476 mmol) and Na2CO3 (371 μL of a 2.0 M aqueous solution, 0.7428 mmol) combined in 1,4-dioxane (3 mL) under N2. Mixture de-gassed (×3 vacuum-N2 cycles) then Pd(PPh3)4 (14 mg, 0.01238 mmol) added. Reaction mixture de-gassed (×3 cycles) and stirred overnight at 110° C. Reaction cooled and partitioned between DCM and water. Aqueous phase extracted with DCM and combined organics dried and concentrated. Residue purified by chromatography (silica, 0-100% EtOAc-petroleum ether gradient elution). Title compound obtained as a yellow solid (186 mg, 88%), taken directly on to deprotection reaction; MS (ES+) 850.0.

WORKUP

后处理

customMixture de-gassed (×3 vacuum-N2 cycles)
customReaction mixture
customde-gassed (×3 cycles)
customReaction
temperaturecooled
custompartitioned between DCM and water
extractionAqueous phase extracted with DCM
customcombined organics dried
concentrationconcentrated
customResidue purified by chromatography (silica, 0-100% EtOAc-petroleum ether gradient elution)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2cbdcdcbf5104f09b638600d61e3a216
来源数据集: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09309250B2
来源说明: uspto-grants-2016_04

反应 SMILES

Br[C:2]1[N:3]=[C:4]2[C:10]([N:11]3[CH2:19][C:18]4[C:13](=[C:14]([Cl:20])[CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])=[CH:9][N:8]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:49]2[CH:54]=[CH:53][C:52]([S:55]([CH:58]3[CH2:63][CH2:62][N:61]([C:64]([O:66]C(C)(C)C)=[O:65])[CH2:60][CH2:59]3)(=[O:57])=[O:56])=[CH:51][CH:50]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12](=[O:21])[N:11]([C:10]1[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:49]4[CH:50]=[CH:51][C:52]([S:55]([CH:58]5[CH2:59][CH2:60][N:61]([C:64]([O:66][C:13]([CH3:18])([CH3:14])[CH3:12])=[O:65])[CH2:62][CH2:63]5)(=[O:56])=[O:57])=[CH:53][CH:54]=4)[N:3]=3)[N:8]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:9]=1)[CH2:19]2