Potassium Carbonate → HCID 12083568, compound

HRID 1357251Notes

Reaction equation

HRID 1357251 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]([CH3:30])[C:15]([C:17]1[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[O:19][C:18]=1[CH2:26][CH2:27][CH2:28][CH3:29])=[O:16])=[CH:7]2.Br[CH2:32][C:33]#[N:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:32][C:33]#[N:34])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:30])[C:15]([C:17]1[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[O:19][C:18]=1[CH2:26][CH2:27][CH2:28][CH3:29])=[O:16])=[CH:7]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587384HCID 86587384, compound

Product 1

HCID 12083568HCID 12083568, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.5587 g, 1.2 mmol), prepared in the previous step, bromoacetonitrile (0.10 mL, 1.44 mmol) and potassium carbonate (0.83 g, 6 mmol) in 10 mL of DMF was stirred under nitrogen at room temperature for 18 h (overnight). The reaction was diluted with ethyl acetate and extracted multiple times with water. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a brown oil. The oil was chromatographed on a 90 g KP-SIL 60 Δ Biotage column using 5% ethyl acetate in methylene chloride as the eluent. Isolation of the desired product gave 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.48 g, 79%) as a clear oil, MS m/z: 505 [M+H]+.

Workup

  1. extractionextracted multiple times with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customto give a brown oil
  5. customThe oil was chromatographed on a 90 g KP-SIL 60 Δ Biotage column

Sources & evidence

ORD record
ord-fb85475685354965805247feca492685
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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