Potassium Carbonate → HCID 12083564, compound

HRID 1357242Notes

Reaction equation

HRID 1357242 reaction equation
[OH:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][NH:13][C:14]([C:16]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][C:17]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:15])[CH:6]=[CH:5]2.Br[CH2:36][C:37]#[N:38].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[C:37]([CH2:36][O:1][C:2]1[C:3]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][NH:13][C:14]([C:16]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][C:17]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:15])[CH:6]=[CH:5]2)#[N:38]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587380HCID 86587380, compound

Product 1

HCID 12083564HCID 12083564, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (6-hydroxy-5-phenyl-naphthalen-2-ylmethyl)-amide (366 mg, 0.813 mmol), prepared in the previous step, bromoacetonitrile (68 μL, 0.976 mmol) and potassium carbonate (562 mg, 4.07 mmol) in 20 mL of DMF was stirred under nitrogen at room temperature for 23 h (overnight). The reaction was diluted with ethyl acetate, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give a brown solid. Purification of the solid on 20 g of silica gel (230-400 mesh) using hexane-ethyl acetate as the eluent gave 2-butyl-benzofuran-3-carboxylic acid (6-cyanomethoxy-5-phenyl-naphthalen-2-ylmethyl)-amide (342 mg, 86%) as a light brown solid, mp 135-138° C.

Workup

  1. extractionextracted multiple times with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customto give a brown solid
  5. customPurification of the solid on 20 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-69f27b28093d4dd893a2b544b5ad092f
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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