Methanesulfonic Acid → HCID 86259916, compound

HRID 1983996Notes

Reaction equation

HRID 1983996 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].CS(O)(=O)=O.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH:5]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 16099887Ethyl (5-fluoro-1H-indol-3-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86259916HCID 86259916, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl (5-fluoro-1H-indol-3-yl)acetate (Bullock et al. J. Am. Chem. Soc. 1951, 73, 5155-5157) (72.5 g, 0.33 mol), 70% methane sulfonic acid (aq) (50 mL) and palladium (5 wt %, dry basis) on activated carbon (20 g) in ethanol (700 mL) was treated with hydrogen at 3 bar and 50° C. for 48 h. The mixture was filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate, and aqueous ammonia was added. The phases were separated, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo (55 g, 75%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionaqueous ammonia was added
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo (55 g, 75%)

Sources & evidence

ORD record
ord-0bf19ef23a1e4fd5b1db15d8dd9e35b8
Source dataset
uspto-grants-2009_06
Patent number
US07544685B2

Reaction notes

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