Ethyl Acetate → HCID 178481818, compound

HRID 271305Notes

Reaction equation

HRID 271305 reaction equation
[C:1]([S:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH2:10][CH:11]2[C:32](=O)[CH:14]([CH2:15][C:16]=1/[CH:17]=[CH:18]/[C:19]1[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:21]([CH3:31])[N:20]=1)[CH2:13][CH2:12]2.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:8][C:9]1[CH2:10][CH:11]2[CH2:12][CH2:13][CH:14](/[C:32]/2=[N:7]/[S:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[O:6])[CH2:15][C:16]=1/[CH:17]=[CH:18]/[C:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:21]([CH3:31])[N:20]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 693100833-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one

Product 1

HCID 178481818HCID 178481818, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butylsulphinamide (3.0, 24 mmol) followed by titanium (IV) ethoxide (4.6 ml, 36 mmol) was added to a stirring solution of the product of Step 3 (4.56 g, 11 mmol) in dry THF (10 ml) and the resulting solution was heated to reflux for 18 hrs. The reaction was poured into a stirring solution of brine (200 ml) and then ethyl acetate (100 ml) was added and the mixture filtered through celite. The filtrate was partitioned and the aqueous layer was further extracted with ethyl acetate (2×50 ml). The combined organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo, to afford N((9Z)-3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-ylidene)-2-methylpropane-2-sulfinamide (5.19 g, 99%). m/z (ES+) 474 (MH)+. Compound taken directly onto next Step.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 18 hrs
  3. filtrationthe mixture filtered through celite
  4. customThe filtrate was partitioned
  5. extractionthe aqueous layer was further extracted with ethyl acetate (2×50 ml)
  6. extractionThe combined organic extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c6df90edbba416b8afb216f35002d16
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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