Sodium Thiosulfate → HCID 57527231, compound

HRID 1452990Notes

Reaction equation

HRID 1452990 reaction equation
C(S[C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[N:13][N:14]([CH3:16])[CH:15]=2)[N:5]=1)C.[CH:24]1C=C(Cl)C=C(C(OO)=O)[CH:25]=1.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.C(Cl)Cl>[CH2:24]([S:35]([C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[N:13][N:14]([CH3:16])[CH:15]=2)[N:5]=1)(=[O:39])=[O:37])[CH3:25]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57527205HCID 57527205, compound

Product 1

HCID 57527231HCID 57527231, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(ethylthio)-6-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)pyridine-3-amine(1.00 g, 3.04 mmol, 1.0 eq.) in THF (100 mL) under nitrogen at 0° C. was added MCPBA (77%, 1.60 g, 9.27 mmol, 3.05 eq.). After 3 h 15 min, 5% aqueous sodium thiosulfate and saturated aqueous NaHCO3 were added, and the solution was stirred for 10 min. CH2Cl2 was then added, and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×), and the organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo. Trituration with EtOAc afforded 2-(ethylsulfonyl)-6-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)pyridine-3amine as a light tan solid (0.94 g, 85% yield).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2201869ff4954770946f3574903b6765
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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