Potassium Carbonate → 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole

HRID 1633615Notes

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.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][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: 55 °C

Procedure

2.05 g (9 mmol) 1-(4-Fluoro-phenyl)-1H-indol-5-ol in 25 ml acetone were treated with 4.7 ml (30 mmol) 1,6-dibromohexane and 4.14 g (30 mmol) K2CO3 powder in 25 ml acetone. The mixture was stirred at 55° C. for 6 h, and at RT for 20 h. Acetone was added, and the suspension filtered. Purification of the crude product with column chromatography with hexane/EtOAc 49:1 yielded 2.4 g (68%) 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole as colorless solid, MS: 389 (M, 1Br, 1Cl).

Workup

waitat RT for 20 h
filtrationthe suspension filtered
customPurification of the crude product with column chromatography with hexane/EtOAc 49:1

Sources & evidence

ORD record: ord-62f9ec50d4ff48f3a026ab2e9b29b156
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503907B2

Reaction notes

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