Ammonium formate → HCID 10270565, compound

HRID 1006419Notes

Reaction equation

HRID 1006419 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([N:18]2[C:19]3[C:15](=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10207065HCID 10207065, compound

Product 1

HCID 10270565HCID 10270565, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 250 mg(0.54 mmole) 4-(4-benzyl-piperazin-1-yl)-1-(4-methoxybenzenesulfonyl)-1H-indole, 500 mg (8 mmole) ammonium formate and 50 mg 10% Pd-C in 20 mL ethanol was heated under reflux for 2 hours. The mixture was filtered through Whatman GF/B and the filtrate was concentrated under reduced pressure. The residue was partitioned between 10 mL 10% sodium carbonate and 25 mL ethyl acetate. The organic phase was washed with 5 ml water, 5 mL saturated sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The 1-(4-Methoxy-benzenesulfonyl)-4-piperazin-1-yl-1H-indole (3) was isolated as the hydrochloride salt from methanol-ethyl acetate-ether, 128 mg, m.p. 209-210° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe mixture was filtered through Whatman GF/B
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was partitioned between 10 mL 10% sodium carbonate and 25 mL ethyl acetate
  6. washThe organic phase was washed with 5 ml water, 5 mL saturated sodium chloride
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d191001cfea74385adf83030e9ff7162
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Reaction notes

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