Triethylamine → HCID 58909944, compound

HRID 1296016Notes

Reaction equation

HRID 1296016 reaction equation
C(N(CC)CC)C.[C:8]([C:12]1[CH:13]=[C:14]([C:24](=[O:26])[CH3:25])[CH:15]=[C:16]([NH:20][CH:21]([CH3:23])[CH3:22])[C:17]=1[O:18][CH3:19])([CH3:11])([CH3:10])[CH3:9].[Br:27]N1C(=O)CCC1=O.C(OCC)(=O)C>O1CCCC1>[Br:27][CH2:25][C:24]([C:14]1[CH:15]=[C:16]([NH:20][CH:21]([CH3:22])[CH3:23])[C:17]([O:18][CH3:19])=[C:12]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:13]=1)=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 58909989HCID 58909989, compound

Product 1

HCID 58909944HCID 58909944, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.63 ml, 4.5 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (0.6 g, 2.3 mmol) were added to a solution of the 1-[3-(tert-butyl)-5-(isopropylamino)-4-methoxyphenyl]-1-ethanone (0.4 g, 1.5 mmol) in tetrahydrofuran (50 ml) while cooling on ice and the mixture was stirred at the same temperature for 30 minutes, after which N-bromosuccinimide (0.53 g, 3.0 mmol) was added and stirring was continued for 30 minutes. Ethyl acetate was added to the reaction mixture, the mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (410 mg) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. washthe mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-17e3883d6cad4031a2b51a634be8b477
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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