1,2-Dibromoethane → Dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine

HRID 38107Notes

Reaction equation

HRID 38107 reaction equation
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:9]1[C:10]([F:28])=[C:11]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:18]([SH:21])[NH:19][N:20]=2)[C:12]([F:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44]Br>CN(C=O)C>[CH2:29]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:18]3[S:21][CH2:43][CH2:44][N:19]3[N:20]=2)[C:10]=1[F:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178505870HCID 178505870, compound

Product 1

HCID 58477092Dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amineYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-Dibenzylamino-2,6-difluoro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (1.26 g, 2.6 mmol) was dissolved in dry DMF (33 mL) under nitrogen atmosphere. Solid potassium carbonate (1.8 g, 13 mmol, 5 eq) was added followed by 1,2-dibromoethane (0.252 mL, 2.86 mmol, 1.1 eq) and the suspension was stirred at room temperature for 4 hours. DMF was then removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate. The organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness. 537 mg of dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine were obtained as white solid (47% over 2 steps).

Workup

  1. customDMF was then removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2cecd265eb72433db66bed924129f72c
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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