Potassium hydroxy sulfite → HCID 86675130, compound

HRID 1504624Notes

Reaction equation

HRID 1504624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:26]([F:29])([F:28])[F:27])/[CH:10]=[CH:11]/[C:12]2[CH:24]=[CH:23][C:15]([C:16]([NH:18][CH:19]3[CH2:22]S[CH2:20]3)=[O:17])=[C:14]([F:25])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[O:31][S:32]([O-:34])=O.[K+]>CC(C)=O.O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:26]([F:29])([F:28])[F:27])/[CH:10]=[CH:11]/[C:12]2[CH:24]=[CH:23][C:15]([C:16]([NH:18][CH:19]3[CH2:22][S:32](=[O:34])(=[O:31])[CH2:20]3)=[O:17])=[C:14]([F:25])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86675131HCID 86675131, compound

Product 1

HCID 86675130HCID 86675130, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirred solution of (E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-fluoro-N-(thietan-3-yl)benzamide (100 mg, 0.2159 mmol) in acetone/water (1:1, 5.0 mL) was added oxone (266 mg, 0.4319 mmol) and the resultant reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined ethyl acetate layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 30% ethyl acetate/pet ether) afforded the title compound as an off white solid (70.0 mg, 66%): 1H NMR (400 MHz, CDCl3) δ 8.07 (t, J=8.4 Hz, 1H), 7.39 (t, J=1.6 Hz, 1H), 7.31 (d, J=1.2 Hz, 1H), 7.26 (m, 2H), 7.23 (m, 2H), 7.19 (d, J=1.6 Hz, 1H), 6.60 (d, J=16.8 Hz, 1H), 6.49 (dd, J=16.8, 7.6 Hz, 1H), 4.90 (m, 1H), 4.64 (m, 2H), 4.14 (m, 2H); ESIMS m/z 493.83 ([M−H]−); IR (thin film) 1527, 1113, 801, 1167, 1321 cm−1.

Workup

  1. customthe resultant reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification
  6. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 30% ethyl acetate/pet ether)

Sources & evidence

ORD record
ord-1555996d29804742ae4304b728665ef4
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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