Dimethylformamide → Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine

HRID 1633706Notes

Reaction equation

HRID 1633706 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2.[CH2:24]([CH2:27][NH2:28])[CH:25]=C.[OH-].[Na+].[CH3:31]N(C=O)C>>[CH2:27]([N:28]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2)[CH3:31])[CH:24]=[CH2:25]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 4437323-Buten-1-amineHCID 186794855-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole

Product 1

HCID 18679530Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amineYield 85%

Conditions

Temperature
80 °C

Procedure

30 mg (0.076 mmol) 5-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole in 0.25 ml DMF were treated with 75 μl of N-Allylmethylamine and stirred at 80° C. during 1 h. The mixture was treated with 0.5M aqueous NaOH and extracted three times with Et2O. Drying of the combined organic layers with Na2SO4, evaporation of the solvent and column chromatography on silica gel with hexane/EtOAc 1:1 gave 25 mg (85%) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine as a light yellow oil, MS: 387 (MH+, 1Cl).

Workup

  1. extractionextracted three times with Et2O
  2. dry with materialDrying of the combined organic layers with Na2SO4, evaporation of the solvent and column chromatography on silica gel with hexane/EtOAc 1:1

Sources & evidence

ORD record
ord-d9649af933174d8c815aa61f0a24261e
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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