Sodium Thiosulfate → Methyl 6-chloro-4-cyano-2-(3-(methylsulfonyl)phenylamino)nicotinate

HRID 516014Notes

Reaction equation

HRID 516014 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17](SC)[CH:16]=2)[N:3]=1.Cl[C:24]1C=C(C=CC=1)C(OO)=O.[O-:34][S:35]([O-:38])(=S)=O.[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([S:35]([CH3:24])(=[O:38])=[O:34])[CH:16]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 58317663Methyl 6-chloro-4-cyano-2-(3-(methylthio)phenylamino)nicotinate

Product 1

HCID 58317716Methyl 6-chloro-4-cyano-2-(3-(methylsulfonyl)phenylamino)nicotinateYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6-chloro-4-cyano-2-(3-(methylthio)phenylamino)nicotinate (291.1 mg, 0.872 mmol) in DMF (10 mL) was added m-chloroperoxybenzoic acid (538.9 mg, 2.405 mmol) at 0° C. The mixture was stirred at RT for 16 h. Aqueous Na2S2O3 (30 mL) was added and the mixture was extracted with EtOAc (2×30 mL). The organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL) and brine (20 mL), were dried over anhydrous Na2SO4, and then filtered (DM1020). The filtrate was concentrated under reduced pressure and the residue was washed with IPE to give the title compound as a yellow solid (158.2 mg, 50%). 1H-NMR (CDCl3) δ ppm 3.11 (s, 3H), 4.07 (s, 3H), 7.10 (s, 1H), 7.57-7.60 (m, 1H), 7.70-7.72 (m, 1H), 7.91-7.93 (m, 1H), 8.25-8.26 (m, 1H), 10.73 (s, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×30 mL)
  2. washThe organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL) and brine (20 mL)
  3. dry with materialwere dried over anhydrous Na2SO4
  4. filtrationfiltered (DM1020)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was washed with IPE

Sources & evidence

ORD record
ord-cc10d71279734e6fba74b5a996c6620f
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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