6-Bromo-1-fluoronaphthalen-2-OL → 2-(6,7-Dimethoxy-4-quinolyloxy)-6-bromo-1-fluoronaphthalene

HRID 1925245Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2OC1C=C2C(=CC=1)C=C(NC(OCC1C=CC=CC=1)=O)C=C2.[Br:37][C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[C:44]([F:48])=[C:43]([OH:49])[CH:42]=[CH:41]2>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:49][C:43]1[CH:42]=[CH:41][C:40]2[C:45](=[CH:46][CH:47]=[C:38]([Br:37])[CH:39]=2)[C:44]=1[F:48]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-quinoline (prepared as in Example 1, Step b)(371 mg, 1.66 mmol), 6-bromo-1-fluoro-naphthalen-2-ol (Step a, 400 mg, 1.66 mmol) and DMAP (203 mg, 1.66 Aldrich) in toluene (in a microwave tube) was heated in a microwave oven (Personal Chemistry, Emrys Optimizer) at 180° C. for 2 h. The mixture was cooled to RT and diluted with 30 mL of EtOAc. The solution was washed with 10 mL of brine twice, dried over Na2SO4 and concentrated in vacuo. The residue was further purified with silica gel column chromatography (40-100% EtOAc in hexanes) to give title compound as a white solid. MS (ESI, pos. ion) m/z: 428.0 (M+1). Mass Calc'd for C21H15BrFNO3: 427.02.

Workup

temperatureThe mixture was cooled to RT
washThe solution was washed with 10 mL of brine twice
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was further purified with silica gel column chromatography (40-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-a425f14724fb463582e6e94f222ea4d7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

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