Sodium Hydroxide → HCID 61299532, compound

HRID 341527Notes

Reaction equation

HRID 341527 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][S:4][C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[F:16][C:2]([F:1])([F:15])[CH2:3][S:4][C:5]1[N:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66803248HCID 66803248, compound2×

Product 1

HCID 61299532HCID 61299532, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 6-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-3-carboxylate (Intermediate 210, 345 mg, 1.37 mmol) in MeOH (10 mL) was added a 2M sodium hydroxide aq. solution (1.37 mL, 2.74 mmol). The resulting reaction mixture was stirred at room temperature for 4 h and then evaporated to dryness. The remaining residue was dissolved in water (20 mL), acidified to pH 4.5 with a 1M aq. HCl solution and extracted with DCM (3×25 mL). Combined organics were dried over magnesium sulfate and evaporated to dryness to afford the title compound as a white solid (300 mg, 93%). Method C HPLC-MS: MH+ requires m/z=238. Found: m/z=238, Rt=1.35 min (98%).

Workup

  1. customThe resulting reaction mixture
  2. customevaporated to dryness
  3. dissolutionThe remaining residue was dissolved in water (20 mL)
  4. extractionextracted with DCM (3×25 mL)
  5. dry with materialCombined organics were dried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-47cf16e5d31c41ec9000249c1570e609
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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