Ammonium formate → 1-Azetidin-3-ylmethyl-6-fluoro-1H-indole

HRID 2056380Notes

Reaction equation

HRID 2056380 reaction equation
C([N:14]1[CH2:17][CH:16]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[CH:21]=[CH:20]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH:14]1[CH2:17][CH:16]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[CH:21]=[CH:20]2)[CH2:15]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 692042621-(1-benzhydryl-azetidin-3-ylmethyl)-6-fluoro-1H-indole

Product 1

HCID 218920951-Azetidin-3-ylmethyl-6-fluoro-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(1-benzhydryl-azetidin-3-ylmethyl)-6-fluoro-1H-indole (0.6 g, 1.6 mmol), palladium on carbon (10%, cat.amount) and ammonium formate (0.2 g, 3.2 mmol) in ethanol (20 mL) was refluxed for 30 min. The mixture was filtered through celite and the solvent removed under vacuum. Diphenylmethane was removed by triturating the residue with ether, methylene chloride and decanting. The remaining product was dried under vacuum. The crude material was directly used in next step without further purification.

Workup

  1. temperaturewas refluxed for 30 min
  2. filtrationThe mixture was filtered through celite
  3. customthe solvent removed under vacuum
  4. customDiphenylmethane was removed
  5. customby triturating the residue with ether, methylene chloride
  6. customdecanting
  7. customThe remaining product was dried under vacuum
  8. customThe crude material was directly used in next step without further purification

Sources & evidence

ORD record
ord-272f6ed19ac9477c98f984bf8ecfd669
Source dataset
uspto-grants-2008_02
Patent number
US07335666B2

Reaction notes

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