Potassium Carbonate → HCID 22281971, compound

HRID 1368661Notes

Reaction equation

HRID 1368661 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([OH:8])[C:3]=1[C:9]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH:26]1[CH2:28][CH2:27]1>CN(C)C=O>[O:13]1[C:12]2[CH:16]=[CH:17][C:9]([C:3]3[C:4]([O:8][CH2:25][CH:26]4[CH2:28][CH2:27]4)=[N:5][N:6]([CH3:7])[C:2]=3[NH2:1])=[CH:10][C:11]=2[O:15][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 178481945HCID 178481945, compound

Product 1

HCID 22281971HCID 22281971, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-amino-4-(1,3-benzodioxol-5-yl)-1-methyl-1H-pyrazol-3-ol (500 mg) (Preparation 46) in anhydrous dimethylformamide (21 ml) under an atmosphere of nitrogen at room temperature was added solid potassium carbonate (980 mg) and bromomethylcyclopropane (230 μl). The mixture was stirred overnight then quenched by the addition of water (100 ml) and a saturated aqueous solution of ammonium chloride (50 ml). The solution was extracted with ethyl acetate (3×40 ml). The organic fraction was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 30 g) eluted with hexane:ethyl acetate (1:2) to yield the title compound as a colourless oil (365 mg).

Workup

  1. customthen quenched by the addition of water (100 ml)
  2. extractionThe solution was extracted with ethyl acetate (3×40 ml)
  3. dry with materialThe organic fraction was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica, 30 g)
  6. washeluted with hexane:ethyl acetate (1:2)

Sources & evidence

ORD record
ord-fb4c9adf15fd43cfa5c4338849e1a701
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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