Potassium Carbonate → 5-(7-Bromo-heptyloxy)-1-(4-fluoro-phenyl)-1H-indole

HRID 1633618Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br>CC(C)=O>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[CH:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

410 mg (1.8 mmol) 1-(4-Fluoro-phenyl)-1H-indol-5-ol in 6 ml acetone were treated with 500 mg (3.6 mmol) powdered K2CO3 and 610 μl (3.6 mmol) 1,7-dibromoheptane. The suspension was stirred at 60° C. overnight, cooled to RT, filtered and concentrated. Column chromatography on silica gel with hexane/EtOAc 49:1 yielded 526 mg (72%) 5-(7-Bromo-heptyloxy)-1-(4-fluoro-phenyl)-1H-indole as colorless solid, mp 63-65° C., MS: 403 (M, 1Br).

Workup

temperaturecooled to RT
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-fc27129c678f421dae5a9b7790a56f76
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503907B2

Reaction notes

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