Ammonium formate → HCID 45098165, compound

HRID 28490Notes

Reaction equation

HRID 28490 reaction equation
C([N:14]1[CH2:17][CH:16]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]#N)[CH:26]=3)[NH: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][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([CH3:28])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69204264HCID 69204264, compound

Product 1

HCID 45098165HCID 45098165, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(1-benzhydryl-azetidin-3-ylmethyl)-1H-indole-5-carbonitrile (8) (0.56 g, 1.5 mmol), palladium on carbon (10%, 0.1 g) and ammonium formate (0.37 g, 5.9 mmol) in ethanol (20 ml) was refluxed for 2 hours. 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. MS ES m/e 200 (M+H)+.

Workup

  1. temperaturewas refluxed for 2 hours
  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

Sources & evidence

ORD record
ord-96d010040adf46b293a90c2be031b00b
Source dataset
uspto-grants-2008_09
Patent number
US07419986B2

Reaction notes

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