Dimethylamine → Methyl 3-dimethylaminomethylbenzofuran-2-carboxylate

HRID 2221443Notes

Reaction equation

HRID 2221443 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][NH:17][CH3:18]>CN(C=O)C.C(OCC)(=O)C>[CH3:16][N:17]([CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13])[CH3:18]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 100838Methyl 3-(bromomethyl)-2-benzofurancarboxylate

Product 1

HCID 59710963Methyl 3-dimethylaminomethylbenzofuran-2-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-bromomethylbenzofuran-2-carboxylate (269 mg, 1.0 mmol) in DMF was added dimethylamine (2M solution in THF, 1.5 ml, 3 mmol). The reaction mixture was stirred for 1-2 h, diluted with ethyl acetate (50 ml), washed twice with saturated aqueous sodium bicarbonate solution (50 ml) and finally with brine (50 ml). The organic extract was dried over sodium sulfate and then concentrated in vacuo. Purification by flash chromatography on silica gel (5% methanol in dichloromethane) gave methyl 3-dimethylaminomethylbenzofuran-2-carboxylate (131 mg, 0.57 mmol).

Workup

  1. washwashed twice with saturated aqueous sodium bicarbonate solution (50 ml) and finally with brine (50 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8623985ee4394cd196963c67d2b710e3
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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