Potassium Carbonate → (6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-2,3-dihydro-1H-indole

HRID 1633671Notes

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](O)=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([O-:21])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]CBr>CC(C)=O>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:18][O:21][CH:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

460 mg (2 mmol) 1-(4-Fluoro-phenyl)-2,3-dihydro-1H-indol-5-ol in 6 ml acetone were treated with 830 mg (6 mmol) powdered K2CO3 and 1 ml (6 mmol) 1,6-dibromohexane. The suspension was stirred at 60° C. for 6 h, cooled to RT, diluted with acetone, filtered and concentrated. Column chromatography on silica gel with a gradient hexane to hexane/EtOAc 19:1 yielded 210 mg (25%) (6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-2,3-dihydro-1H-indole as yellow oil, MS: 392(MH+, 1Br).

Workup

temperaturecooled to RT
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d7c2dcd6c21f40408a54194e528230f5
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503907B2

Reaction notes

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