Morpholine → 6-bromo-N-(4-methoxybenzyl)-3-morpholinoquinolin-2-amine

HRID 1028934Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:6](I)=[CH:5]2.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(C1CCCCC1=O)(=O)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:6]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[CH:5]2

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine (710 mg, 1.5 mmol), morpholine (1.9 mL, 22.7 mmol), Cu(I)(14.4 mg, 0.08 mmol), cesium carbonate (986 mg, 3.0 mmol), 2-isobutyrylcyclohexanone (50.9 mg, 0.30 mmol) and DMF (10 mL) was heated to 125° C. in a microwave unit for 20 min. The mixture was concentrated in vacuo then partioned the crude product between EtOAc and water. The organic layer was washed with water and brine 3× each, dried over MgSO4 and concentrated in vacuo to give an orange colored oil. This material was purified by silica flash chromatography (0-5% MeOH/DCM) to give 6-bromo-N-(4-methoxybenzyl)-3-morpholinoquinolin-2-amine as a yellow colored oil.

Workup

concentrationThe mixture was concentrated in vacuo
washThe organic layer was washed with water and brine 3× each,
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an orange colored oil
customThis material was purified by silica flash chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record: ord-a53dfdc593554c3d8facad6201507d44
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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