Boron trifluoride etherate → HCID 69195683, compound

HRID 268652Notes

Reaction equation

HRID 268652 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][CH3:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:13][CH2:14][OH:15].B(F)(F)F.CCOCC.[C:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(=O)[CH2:26][CH3:27]>ClCCl>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][C:25]1([CH2:26][CH3:27])[C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH2:13][CH2:14][O:15]1)=[CH:3][C:2]([Br:1])=[CH:10][C:9]=3[CH2:11][CH3:12])[CH3:34]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 78656Ethyl 3-oxovalerateHCID 69199097HCID 69199097, compound

Product 1

HCID 69195683HCID 69195683, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-bromo-7-ethyl-1H-indol-3-yl)-ethanol in dichloromethane at room temperature under nitrogen was added boron trifluoride diethyl etherate (0.809 g, 5.7 mmol), followed by ethyl propionylacetate (1.038 g, 7.2 mmol). The reaction mixture was stirred at room temperature for 5 hours. It was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 15-20% ethyl acetate/hexane) to give the title compound (0.994 g, 53% yield). ES-MS (m/z) 394 [M+1]+, 392 [M−1]−.

Workup

  1. customIt was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel, 15-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b69cab40b5ed4237a9aa00f085c747cf
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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