Potassium hydroxy sulfite → HCID 118045499, compound

HRID 596078Notes

Reaction equation

HRID 596078 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([O-:14])=[O:13])=[C:10]([F:17])[CH:9]=2)=[CH:6][C:5]([C:18]2[CH2:19][CH2:20]S[CH2:22][CH:23]=2)=[CH:4][N:3]=1.OO[S:26]([O-:28])=O.[K+]>CC(C)=O.O.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:14][C:5]([CH3:18])([CH3:6])[CH3:4])=[O:13])=[C:10]([F:17])[CH:9]=2)=[CH:6][C:5]([C:18]2[CH2:19][CH2:20][S:26](=[O:28])[CH2:22][CH:23]=2)=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 131734624HCID 131734624, compound

Product 1

HCID 118045499HCID 118045499, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of 4-(2-amino-5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-3-yl)-2-fluorobenzoate in acetone (20 mL) was treated with a solution of oxone (227 mg, 0.369 mmol) in water (5 mL). After 20 min, the reaction was diluted with ethyl acetate (50 mL) and water (50 mL). The layers were separated and the aqueous layer was washed with ethyl acetate (50 mL). The combined organics were washed with water (30 mL) and brine (30 mL), dried over magnesium sulfate, filtered and concentrated to provide tert-butyl 4-(2-amino-5-(1-oxido-3,6-dihydro-2H-thiopyran-4-yl)pyridin-3-yl)-2-fluorobenzoate (220 mg, 74% yield). LCMS (m/z): 403.5 (MH+), 0.66 min.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with ethyl acetate (50 mL)
  3. washThe combined organics were washed with water (30 mL) and brine (30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f66f6d672e7c47e8a05fdfdb1475a679
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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