HRID522970

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1

HCID634876

2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

C44H32P2

HCID2735179

3-methylsulfonylaniline Hydrochloride

C7H10ClNO2S

结构：CC(C)(C)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(Br)nc12

HCID71575645

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(Nc3cccc(S(C)(=O)=O)c3)nc12

HCID131735556

未命名化合物

收率 34%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

催化剂HCID23676156

Sodium t-butoxide

C4H9NaO

溶剂HCID962

Water

H2O

溶剂HCID1140

Toluene

C7H8

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 140 °C

PROCEDURE

实验过程

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 mol), 3-(methylsulfonyl)aniline hydrochloride (109 mg, 526 mol), BINAP (10.9 mg, 17.5 mol), palladium (II) acetate (19.7 mg, 87.7 mol) and sodium tert-butoxide (101 mg, 1.05 mmol, Eq: 3) in DMF (1 mL) and toluene (500 μL) was heated in a microwave at 140° C. for 20 min. The reaction mixture was diluted with water then extracted into ethyl acetate (3×). The combined organic extracts were washed with brine then dried over magnesium sulfate. Purification by chromatography (silica, 20-50% ethyl acetate in hexanes) gave N-tert-butyl-2-(3-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (61 mg, 118 mol, 34%) as a brown gum. (EI/CI) m/z: 518.3 [M+H].

WORKUP

后处理

extractionthen extracted into ethyl acetate (3×)
washThe combined organic extracts were washed with brine
dry with materialthen dried over magnesium sulfate
customPurification by chromatography (silica, 20-50% ethyl acetate in hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6b2edba179bb4c5baab69ea1ec89dedf
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09334278B2
来源说明: uspto-grants-2016_05

反应 SMILES

Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]2=[N:6][CH:7]=1.Cl.[CH3:27][S:28]([C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34])(=[O:30])=[O:29].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)([O-])C.[Na+]>[C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:34][C:33]3[CH:35]=[CH:36][CH:37]=[C:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH:32]=3)[N:3]=2)[N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]