Potassium Carbonate → HCID 12083565, compound

HRID 1357243Notes

Reaction equation

HRID 1357243 reaction equation
[OH:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[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[CH2:38][C:39]#[N:40].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[C:39]([CH2:38][O:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[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)#[N:40]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587381HCID 86587381, compound

Product 1

HCID 12083565HCID 12083565, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid [6-hydroxy-5-(4-methoxy-phenyl)-naphthalen-2-ylmethyl]-amide (301 mg, 0.63 mmol), prepared in the previous step, bromoacetonitrile (52 μL, 0.75 mmol) and potassium carbonate (434 mg, 3.14 mmol) in 20 mL of DMF was stirred under nitrogen at room temperature for 21 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 2-butyl-benzofuran-3-carboxylic acid [6-cyanomethoxy-5-(4-methoxy-phenyl)-naphthalen-2-ylmethyl]-amide (325 mg, 99%) as a brown solid, mp 139-142° C.

Workup

  1. extractionextracted multiple times with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a0f197b40c844b6aa68a241e49d873af
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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