Potassium Carbonate → HCID 12083584, compound

HRID 1357290Notes

Reaction equation

HRID 1357290 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:34])[C:15]([C:17]1[O:18][C:19]3[CH:33]=[CH:32][CH:31]=[CH:30][C:20]=3[C:21]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:16])=[CH:7]2.Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:40][O:39][C:37](=[O:38])[CH2:36][O:12][C:11]1[CH:10]=[CH:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([CH2:13][N:14]([CH3:34])[C:15]([C:17]3[O:18][C:19]4[CH:33]=[CH:32][CH:31]=[CH:30][C:20]=4[C:21]=3[CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:16])[CH:7]=2)[C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 86587395HCID 86587395, compound

Product 1

HCID 12083584HCID 12083584, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-phenylethyl-benzofuran-2-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide, prepared in step 4 of Example 45, methyl bromoacetate (260 μL, 2.75 mmol) and potassium carbonate (1.58 g, 11.96 mmol) in 25 mL of DMF was stirred under nitrogen at room temperature 16 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give (1-bromo-6-{[methyl-(3-phenethyl-benzofuran-2-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-acetic acid methyl ester (1.29 g, 96%) as a light brown foam, MS m/z: 586 [M+H]+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionextracted multiple times with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c46493f0adac4ba78ff7f000af3dfdfd
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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