Sodium Sulfite → HCID 72205539, compound

HRID 2204387Notes

Reaction equation

HRID 2204387 reaction equation
[O-]S([C:5]([F:8])(F)F)(=O)=O.F[N+]1C(C)=CC(C)=CC=1C.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:53])=[C:24]([N:26]2[C:33](=[O:34])[C:32]3C=[C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[O:41][CH3:42])[N:29]([CH:43]([CH3:45])[CH3:44])[C:28]=3[CH:27]2[C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[CH:25]=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:53])=[C:24]([N:26]2[C:33](=[O:34])[C:32]3[C:5]([F:8])=[C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[O:41][CH3:42])[N:29]([CH:43]([CH3:45])[CH3:44])[C:28]=3[CH:27]2[C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 72206099HCID 72206099, compound

Product 1

HCID 72205539HCID 72205539, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

1-Fluoro-2,4,6-trimethyl-pyridinium triflate (0.902 mmol) was added to a solution of 5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-2-(2-methoxy-phenyl)-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Example 9) (0.301 mmol) in 1,2-dichloroethane (4 mL) and then the mixture was heated to 80° C. in the dark. After 16 h, the reaction mixture was cooled to rt, poured into a 2% aqueous solution of sodium sulfite and extracted with EtOAc (2×). The combined organic layers were successively washed with 1M aqueous citric acid, 1M aqueous NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a beige foam. ESI-MS: tR=1.40 min, [M]+523/525 (LC-MS 1); TLC: Rf=0.25 (1:2 EtOAc/heptanes).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were successively washed with 1M aqueous citric acid, 1M aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-d79355ee5d6642c3bce88dc1d6dc6344
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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