Ammonium formate → HCID 45098165, compound

HRID 720394Notes

Reaction equation

HRID 720394 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-75979e73b4dd4ab69c65bd6551259da8
Source dataset
uspto-grants-2006_11
Patent number
US07135479B2

Reaction notes

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