Dimethylformamide → HCID 10805854, compound

HRID 1069652Notes

Reaction equation

HRID 1069652 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1)[CH3:2].CN(C=O)C.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=1)[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 105138025-Methoxy-1H-indole-3-acetic acid ethyl ester

Product 1

HCID 10805854HCID 10805854, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Methoxy-1H-indole-3-acetic acid ethyl ester (10.1 g, 41 mmol) was dissolved in 50 mL of THF and 200 mL of DMF and 1.8 g (45 mmol) of 60% NaH/mineral oil were added in portions with cooling. After 0.17 hours, 5 mL (42 mmol) of benzyl bromide was added and stirring maintained for 1.5 hours. The mixture was diluted with water and ethyl acetate, the organic layer separated, washed with water, brine and dried (Na2SO4). The solution was evaporated at reduced pressure and the residue chromatographed on silica gel eluting with a gradient, 25% ethyl acetate/hexane→40% ethyl acetate/hexane, to give 10.8 g (82% yield) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester.

Workup

  1. temperaturewith cooling
  2. temperaturemaintained for 1.5 hours
  3. customthe organic layer separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solution was evaporated at reduced pressure
  7. customthe residue chromatographed on silica gel eluting with a gradient, 25% ethyl acetate/hexane→40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-568b0a439dba470d8a06677c45589ceb
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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