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

HRID 38084

Reaction equation

HRID 38084 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]([SH:14])[NH:12][N:13]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29]Br>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]3[S:14][CH2:28][CH2:29][N:12]3[N:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178489941HCID 178489941, compound

Product 1

HCID 674229736-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazoleYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-Methoxy-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (630 mg, 2.22 mmol) was dissolved in dry DMF (22 mL) under nitrogen atmosphere. Solid potassium carbonate (1.5 g, 11.1 mmol, 5 eq) was added followed by 1,2-dibromoethane (0.192 mL, 2.22 mmol, 1 eq) and the suspension was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure, diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated to dryness to give 420 mg (61% over two steps) of crude 6-(3-methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole which was used without further purification in the following step.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4c0ef89d3b0b41639c930e4c95a53739
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

Loading…