Methyl 2-((4,6-difluoro-1H-indol-3-yl)thio)acetate → 2-((4,6-difluoro-1H-indol-3-yl)thio)acetic acid

HRID 1621265Notes

Reaction equation

HRID 1621265 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:5][NH:6]2>O1CCCC1.[Li+].[OH-].C(OCC)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5][NH:6]2

Participants

5

Reactant 1

HCID 68004081Methyl 2-((4,6-difluoro-1H-indol-3-yl)thio)acetate

Product 1

HCID 680039162-((4,6-difluoro-1H-indol-3-yl)thio)acetic acidYield 98%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((4,6-difluoro-1H-indol-3-yl)thio)acetate (253 mg, 0.98 mmol) from Step A was dissolved in a mixture of tetrahydrofuran (8 mL) and 2.0 M aqueous LiOH (2 mL), then stirred vigorously at ambient temperature for 30 minutes. Tetrahydrofuran was removed in vacuo, the aqueous layer neutralized with 1.2 N HCl and extracted with CH2Cl2. The organic layer was dried over magnesium sulfate and removed in vacuo to produce an oily residue. After diluting the residue with diethylether and removing the solvent in vacuo a solid formed which was the desired product (232 mg, 0.95 mmol, 98% yield). LCMS>99% at 254 nm, RT=1.17 min, m/z=244 (M+1).

Workup

  1. customTetrahydrofuran was removed in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customremoved in vacuo
  5. customto produce an oily residue
  6. customremoving the solvent in vacuo a solid
  7. customformed which

Sources & evidence

ORD record
ord-b1b6b9d17c6e45a0a3b8cc8b2af85272
Source dataset
uspto-grants-2014_07
Patent number
US08772509B2

Reaction notes

Loading…