Potassium Carbonate → HCID 57658838, compound

HRID 910019Notes

Reaction equation

HRID 910019 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)=[O:9])[CH:7]=1.Br[CH2:23][C:24]#[N:25].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:23][C:24]#[N:25])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 688693(5-Bromo-2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone

Product 1

HCID 57658838HCID 57658838, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(5-Bromo-2-hydroxy-phenyl)-(1-phenyl-1H-pyrazol-4-yl)ketone (342 mg) was added bromoacetonitrile (122 mg), acetone (2 mL) and K2CO3 (140 mg), and the reaction was stirred for 24 h. The reaction mixture was concentrated and the residue was partitioned between water and EtOAc. The organic phase was washed with brine, dried (MgSO4) and concentrated to give 383 mg (100%) yellow solid, that was used directly in the next step: LC/MS (an10p8): Rt 4.39 min, m/z 381.5 [M+1]+; 1H NMR (CDCl3): δ 4.80 (s, 2H), 7.07 (d, J=8.7 Hz, 1H), 7.35-7.42 (m, 1H), 7.45-7.54 (m, 2H), 7.60-7.69 (m, 2H), 7.69-7.75 (m, 2H), 8.03 (s, 1H), 8.31 (s, 1H); 13C NMR (CDCl3): δ 55.2, 114.7, 116.6, 116.7, 120.1, 125.1, 128.2, 129.9, 131.0, 132.6, 133.2, 135.0, 139.3, 142.7, 153.0, 186.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between water and EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c058c00e9474c749ac7f73c27964ae9
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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