Methanol → HCID 86659858, compound

HRID 2360121Notes

Reaction equation

HRID 2360121 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:7]=[CH:6]2.B(Br)(Br)Br.ClCCl.CO.C([O-])(O)=O.[Na+]>ClCCl>[CH2:12]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 82087709HCID 82087709, compound

Product 1

HCID 86659858HCID 86659858, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-1-phenethylindole (95 mg, 0.38 mmol) in 1.9 mL of dry dichloromethane was added boron tribromide-dichloromethane solution (4 M, 0.47 mL, 1.9 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, methanol (1 mL) was added with additional stirring at room temperature for 5 min. After the reaction mixture was neutralized by saturated NaHCO3 aqueous solution, the solution was extracted with ethyl acetate. The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5) to obtain the title compound (25.3 mg, 28%).

Workup

  1. stirringwith additional stirring at room temperature for 5 min
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)

Sources & evidence

ORD record
ord-2f4e49fc8ca44bb187bbd7567659bdc9
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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