1,2-Dibromoethane → 6-(3-Nitro-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

HRID 38072Notes

Reaction equation

HRID 38072 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:12]([SH:15])[NH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30]Br>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:12]3[S:15][CH2:29][CH2:30][N:13]3[N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178526614HCID 178526614, compound

Product 1

HCID 674230366-(3-Nitro-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazoleYield 86.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Nitro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (298 mg, 1.0 mmol) was dissolved in dry DMF (12.5 mL) under nitrogen atmosphere. Solid potassium carbonate (690 mg, 5 mmol, 5 eq) was added followed by 1,2-dibromoethane (0.086 mL, 1 mmol, 1 eq) and the suspension was stirred at room temperature for 3 hours. The reaction mixture was then diluted with ethyl acetate (60 mL) and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. 280 mg of 6-(3-nitro-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole were obtained as an off-white solid (87%).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2fdef811f2f4a3a9bbd7c7cc3e606e6
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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