Sodium Iodide → 2-(4-fluorophenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 628461Notes

Reaction equation

HRID 628461 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[NH:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:10]=1)(=O)=O.[I-].[Na+].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:10]=[C:9]3[CH2:8][CH2:7][CH2:6][N:13]3[N:12]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 894884743-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]propyl methanesulfonate

Product 1

HCID 674372812-(4-fluorophenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of crude 3-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]propyl methanesulfonate (52 g, 0.122 mol), in 300 mL N,N′-Dimethylformamide is added at 10° C. sodium iodide (1.84 g, 12.2 mmol). Then, sodium hydride (60%, 5.4 g, 0.134 mol) is added portionwise and the mixture is stirred for 30 min at 10° C. followed by 1 h at room temperature. To the resulting brown suspension is added saturated ammonium chloride and the mixture is extracted with ethyl acetate. The extracts are dried and evaporated in vacuo. The obtained crude product is purified by trituration with 50 mL water+50 mL n-hexane. After drying of the solid in vacuo 22.9 g (90%) of the product is obtained and is being used without further purification in the next step.

Workup

  1. waitfollowed by 1 h at room temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. customThe extracts are dried
  4. customevaporated in vacuo
  5. customThe obtained crude product
  6. customis purified by trituration with 50 mL water+50 mL n-hexane
  7. dry with materialAfter drying of the solid in vacuo 22.9 g (90%) of the product
  8. customis obtained
  9. customis being used without further purification in the next step

Sources & evidence

ORD record
ord-8ebacf6edac14f43937d19208f0d2d0c
Source dataset
uspto-grants-2016_04
Patent number
US09314026B2

Reaction notes

Loading…