Bromide ion → HCID 12083562, compound

HRID 1357238Notes

Reaction equation

HRID 1357238 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][NH:14][C:15]([C:17]1[CH:21]=[NH+:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]=1[CH2:28][CH2:29][CH3:30])=[O:16])=[CH:7]2.[Br-].Br[CH2:33][C:34]#[N:35].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CN(C=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:33][C:34]#[N:35])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][NH:14][C:15]([C:17]1[CH:21]=[N:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]=1[CH2:28][CH2:29][CH3:30])=[O:16])=[CH:7]2

Participants

7

Reactant 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 178439452HCID 178439452, compound

Product 1

HCID 12083562HCID 12083562, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[(5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-carbamoyl]-2-phenyl-3-propyl-2H-pyrazol-1-ium; bromide (0.30 g, 0.646 mmol), prepared in the previous step, bromoacetonitrile (0.054 mL, 0.775 mmol), potassium carbonate (0.446 g, 3.23 mmol) and 10 mL of DMF was stirred under nitrogen at room temperature overnight. The reaction was diluted with ethyl acetate and extracted multiple times with water and with a saturated sodium chloride solution. The organic layer was separated, 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 15% ethyl acetate in methylene chloride as the eluent. All fractions containing product were combined and the solvent removed under reduced pressure to give 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-amide (0.196 g, 60%) as a light yellow solid, mp 175-176° C.

Workup

  1. extractionextracted multiple times with water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customto give a brown oil
  6. customThe oil was chromatographed on a 90 g KP-SIL 60 Δ Biotage column
  7. additionAll fractions containing product
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c9cca1b10298433290eb38868839ab7f
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…