Potassium Carbonate → HCID 12083572, compound

HRID 1357264Notes

Reaction equation

HRID 1357264 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][N:13]([CH3:29])[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[CH2:31][C:32]#[N:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[C:32]([CH2:31][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][N:13]([CH3:29])[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:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587388HCID 86587388, compound

Product 1

HCID 12083572HCID 12083572, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.90 g, 2.32 mmol), prepared in step-4 of Example 31, bromoacetonitrile (0.194 mL, 2.79 mmol) and potassium carbonate (1.6 g, 11.6 mmol) in 10 mL DMF was stirred under nitrogen at room temperature for 24 h (overnight). The reaction was diluted with ethyl acetate and extracted five times with water. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-benzofuran-3-carboxylic acid (6-cyanomethoxy-naphthalen-2ylmethyl)-methyl-amide (0.94 g, 95%) as a brown oil, MS m/z: 427 [M+H]+.

Workup

  1. extractionextracted five times with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-21348c05a2e6433d83b9968592a4a40b
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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