Sodium Bicarbonate → HCID 86713000, compound

HRID 521943Notes

Reaction equation

HRID 521943 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2(O)[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[N:3]1.COCCN(S(F)(F)[F:28])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[F:28][C:7]1([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][C:5]=2[N+:15]([O-:17])=[O:16])[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86680017(Z)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enol

Product 1

HCID 86713000HCID 86713000, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enol (1.35 g, 5.70 mmol) in dry DCM (60 mL) was added dropwise a solution of deoxo-Fluor® (50% in THF, 6.2 mL, 17.1 mmol) and the reaction mixture was stirred at room temperature for 90 min. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution (70 mL) was added, dropwise initially, and extracted with DCM (100 mL). The organic layer was separated, dried over MgSO4, and concentrated under reduced pressure. Purification via silica gel column chromatography (15-20% EtOAc/hexane) gave (Z)-5-(1-fluorocyclohept-4-enyl)-1-methyl-4-nitro-1H-pyrazole as an off-white solid (615 mg, 45%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractiondropwise initially, and extracted with DCM (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification via silica gel column chromatography (15-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-3043319cc2794103b996b09ab8298eca
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

Loading…