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

HRID 1483189
Notes
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Reaction equation

HRID 1483189 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a741ebfedc054e29aee943e3e92f4be6
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09416121B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes