1,2-Dibromoethane → HCID 67424308, compound

HRID 38089Notes

Reaction equation

HRID 38089 reaction equation
[SH:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[C:3]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29]Br>CN(C=O)C>[N:18]1[CH:19]=[CH:20][C:15]([C:3]2[C:4]([C:7]3[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=3)[C:10]#[N:11])=[N:5][N:6]3[CH2:29][CH2:28][S:1][C:2]=23)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178509728HCID 178509728, compound

Product 1

HCID 67424308HCID 67424308, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(5-Mercapto-4-pyridin-4-yl-1H-pyrazol-3-yl)-benzonitrile (4.59 g, 16.1 mmol) was dissolved in dry DMF (200 mL) under nitrogen atmosphere. Solid potassium carbonate (11.1 g, 80.5 mmol, 5 eq) was added followed by 1,2-dibromoethane (1.53 mL, 17.71 mmol, 1.1 eq) and the suspension was stirred at room temperature for 4 hours. The reaction mixture was then concentrated under reduced pressure and diluted with ethyl acetate. It was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was treated with methanol and the solid was filtered and discarded. The mother liquor was evaporated to dryness and purified by chromatography on silica gel (eluant DCM/MeOH 97:3) to give 1.27 g of 3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzonitrile as a white solid (26% over 2 steps).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washIt was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude product was treated with methanol
  7. filtrationthe solid was filtered
  8. customThe mother liquor was evaporated to dryness
  9. custompurified by chromatography on silica gel (eluant DCM/MeOH 97:3)

Sources & evidence

ORD record
ord-80aec1115d804fa5ade63c9a3579766b
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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