Tetrabutylammonium Fluoride → HCID 86699439, compound

HRID 1777667Notes

Reaction equation

HRID 1777667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]([Si](C)(C)C)=[C:5]2[CH2:16][CH2:17][NH:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH:21]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:16][CH2:17][NH:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86699389N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide

Product 1

HCID 86699439HCID 86699439, compoundYield 47%

Procedure

A mixture of N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide (0.045 g; 0.088 mmol) and tetrabutyl ammonium fluoride (0.263 mL, 1N in THF) was stirred at room temperature for 18 hours and concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The organic layer was dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane) to afford 0.018 g (47%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and dichloromethane
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-81c958bb4e54434a8a26683a21a0ddfa
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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