HRID393298

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID22043

Benzoic acid, 4-bromo-, ethyl ester

C9H9BrO2

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

HCID634876

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

C44H32P2

结构：CCN1c2ncc(CCOc3ccc(N)cc3C)cc2C(=O)N(C)c2cccnc21

HCID22648858

未命名化合物

HCID178418730

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)c1ccc(Nc2ccc(OCCc3cnc4c(c3)C(=O)N(C)c3cccnc3N4CC)c(C)c2)cc1

HCID22648876

未命名化合物

收率 40%

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID1140

Toluene

C7H8

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 105 °C

PROCEDURE

实验过程

A degassed mixture of 11-ethyl-5,11-dihydro-8-[2-(4-amino-2-methylphenoxy)ethyl]-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (100 mg, 0.25 mmol), ethyl 4-bromobenzoate (61.0 μL, 0.37 mmol), t-BuONa (36.0 mg, 0.37 mmol), Pd2(dba)3 (2.5 mg, 2.7 μmol) and (+/−)-BINAP (5.0 mg, 8.0 1mol) in toluene (8 mL) was heated to 105° C. under nitrogen for 48 h. The cooled reaction mixture was diluted with EtOAc, filtered through a short pad of diatomaceous earth and was concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to give the title compound (55 mg, 40% yield) as a white solid.

WORKUP

后处理

customThe cooled reaction mixture
filtrationfiltered through a short pad of diatomaceous earth
concentrationwas concentrated under reduced pressure
customThe residue was purified by flash chromatography (Hexane:EtOAc, 1:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-fd40204fe0fd4cae9da61a2ce2d7ae93
来源数据集: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06806265B2
来源说明: uspto-grants-2004_10

反应 SMILES

[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=3[CH3:24])=[CH:13][C:8]=2[C:7](=[O:25])[N:6]([CH3:26])[C:5]2[CH:27]=[CH:28][CH:29]=[N:30][C:4]1=2)[CH3:2].Br[C:32]1[CH:42]=[CH:41][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][CH:33]=1.C(O[Na])(C)(C)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:32]4[CH:42]=[CH:41][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][CH:33]=4)=[CH:19][C:18]=3[CH3:24])=[CH:13][C:8]=2[C:7](=[O:25])[N:6]([CH3:26])[C:5]2[CH:27]=[CH:28][CH:29]=[N:30][C:4]1=2)[CH3:2]