2-Methoxyethylamine → {6-Bromo-3-[(2-methoxy-ethylamino)methyl]-benzofuran-2yl}(2,4-dichlorophenyl)-methanone

HRID 29243Notes

Reaction equation

HRID 29243 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].[Br:12][C:13]1[CH:33]=[CH:32][C:16]2[C:17]([CH2:30]Br)=[C:18]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[O:21])[O:19][C:15]=2[CH:14]=1>C1COCC1>[Br:12][C:13]1[CH:33]=[CH:32][C:16]2[C:17]([CH2:30][NH:5][CH2:4][CH2:3][O:2][CH3:1])=[C:18]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[O:21])[O:19][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 59788888(6-Bromo-3-bromomethyl-benzofuran-2-yl)(2,4-dichlorophenyl)-methanone

Product 1

HCID 59788886{6-Bromo-3-[(2-methoxy-ethylamino)methyl]-benzofuran-2yl}(2,4-dichlorophenyl)-methanoneYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxyethylamine (118 mg, 1.57 mmol) in THF (6 mL) at 0° C. was added potassium carbonate followed by slow addition of (6-bromo-3-bromomethyl-benzofuran-2-yl)-(2,4-dichlorophenyl)-methanone (660 mg, 1.43 mmol) in several portions. The reaction mixture was stirred at rt for 2 h, and the resulting precipitate was removed by filtration and the filtrate was concentrated. The crude residue was purified by column chromatography (30-50% ethyl acetate in hexanes) giving the desired product (315 mg, 44% yield) as a light yellow viscous oil. 1H-NMR (acetone): δ 8.05 (d, 1H), 7.78 (d, 1H), 7.66 (m, 2H), 7.56 (dd, 1H), 7.50 (dd, 1H), 4.25 (s, 2H), 3.41 (t, 2H), 3.25 (s, 3H), 2.74 (t, 2H). LC-MS RT=2.71 min; [M+H]+=456.0.

Workup

  1. customthe resulting precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was purified by column chromatography (30-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a94916f71057437ca72e5a8b51aad90f
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Reaction notes

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