Pyridine → (+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-(n-4-chlorophenyl)aminoquinoline

HRID 1349539Notes

Reaction equation

[CH3:1][N:2]([CH3:23])[C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH2:19])[CH2:11][C@@H:10]2[CH3:20])=[O:8])=[CH:5][CH:4]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.N1C=CC=CC=1.C(OCC)(=O)C>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:23][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH:19][C:28]3[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=3)[CH2:11][C@@H:10]2[CH3:20])=[O:8])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (±)-cis-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-aminoquinoline (423 mg, 1.36 mmol) in DMF (15 mL, dry) was added 4-chlorophenylboronic acid (425 mg, 2.72 mmol), pyridine (322 mg, 330 uL, 4.08 mmol) and copper(II)acetate (494 mg, 2.72 mmol). The heterogeneous green mixture was stirred open to air for 1 h and then warmed to 60° C. and stirred over night (14 h). The mixture was then cooled to rt, poured into rapidly stirred ethyl acetate (150 mL); solids were removed by filtration. The extracts were washed several times with water and then once with brine.

Workup

stirringstirred over night (14 h)
temperatureThe mixture was then cooled to rt
customsolids were removed by filtration
washThe extracts were washed several times with water

Sources & evidence

ORD record: ord-a53350fd23074cf28f78915726b1a480
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211672B2

Reaction notes

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