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Morpholine → 4-(3-Aminophenyl)-5,7-dimethyl-6-[4-(morpholinomethyl)phenyl]chromen-2-one

HRID 1483189
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HRID 1483189 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:20])=[C:15](Br)[C:16]=3[CH3:18])[O:11][C:10](=[O:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2].O.CCOC(C)=O.O1CCOCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:20])=[C:15]([C:27]4[CH:28]=[CH:29][C:24]([CH2:23][N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[CH:25][CH:26]=4)[C:16]=3[CH3:18])[O:11][C:10](=[O:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27355934-(Bromomethyl)phenylboronic acidHCID 894779214-(3-Aminophenyl)-6-bromo-5,7-dimethyl-2H-chromen-2-one

생성물 1

HCID 715489304-(3-Aminophenyl)-5,7-dimethyl-6-[4-(morpholinomethyl)phenyl]chromen-2-one수율 75%

시약·촉매·용매 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매2회
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

A mixture of 4-(3-aminophenyl)-6-bromo-5,7-dimethyl-2H-chromen-2-one (6-4) (25 mg, 0.073 mmol), 4-(bromomethyl)phenylboronic acid (24 mg, 0.11 mmol), morpholine (30 μL, 0.35 mmol), K2CO3 (18 mg, 0.13 mmol), dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II)-dichloromethane adduct (6 mg, 0.007 mmol), water (0.3 mL) and 1,4-dioxane (2.7 mL) was heated in a sealed vial in a microwave reactor at 130° C. for 30 min. To the mixture was added EtOAc and water, and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (hexanes: EtOAc=1:1˜0:1) to afford the title compound 6-5 (24 mg, 75% yield) as a yellow oil.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexanes: EtOAc=1:1˜0:1)

출처 및 근거

ORD 기록
ord-a741ebfedc054e29aee943e3e92f4be6
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09416121B2

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