Potassium hydroxy sulfite → HCID 70655298, compound

HRID 705217Notes

Reaction equation

HRID 705217 reaction equation
S1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([C:14]3[N:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:16][C:15]=3[F:24])=[C:9]([F:25])[CH:8]=2)[CH2:3][CH2:2]1.O[O:27][S:28]([O-:30])=O.[K+]>C(Cl)Cl>[O:27]=[S:28]1(=[O:30])[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([C:14]3[N:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:16][C:15]=3[F:24])=[C:9]([F:25])[CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfite2×HCID 70654855HCID 70654855, compound

Product 1

HCID 70655298HCID 70655298, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 6-(4-(3,6-dihydro-2H-thiopyran-4-yl)-2,6-difluorophenyl)-5-fluoropicolinate (1.0 equiv.) in DCM (0.10 M) at rt was added oxone (6.0 equiv.) in one portion. The resulting mixture was stirred at RT overnight, and then refluxed at 40° C. for 4 hrs. 10.0 equiv. of oxone were added and the reaction was allowed to stir at 40° C. over the weekend. The reaction mixture was then diluted with DCM and washed with water the aqueous layer was then separated and extracted with DCM. The combined organic were then dried over MgSO4 and concentrated in vacuo to yield methyl 6-(4-(1,1-dioxido-3,6-dihydro-2H-thiopyran-4-yl)-2,6-difluorophenyl)-5-fluoropicolinate in 100% yield. LC/MS=398.0 (M+H), Rt=0.76 min.

Workup

  1. temperaturerefluxed at 40° C. for 4 hrs
  2. stirringto stir at 40° C. over the weekend
  3. washwashed with water the aqueous layer
  4. customwas then separated
  5. extractionextracted with DCM
  6. dry with materialThe combined organic were then dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02f5de32dd1b463cb45729db7dc17444
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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