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

HRID 1483189Notes

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

Participants

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

extractionextracted with EtOAc
washThe organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
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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