HCID 14986115, compound → HCID 14986118, compound

HRID 2247860Notes

Reaction equation

HRID 2247860 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 14986115HCID 14986115, compound

Product 1

HCID 14986118HCID 14986118, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

In a 500 ml Parr hydrogenation bottle was suspended 1.0 g of 5% Pd/C in 25 ml ethanol, followed by a suspension of 2,3-dihydro-1-(3-nitro-4-pyridinyl)-1H-indole (4.7 g) in 125 ml ethanol. After shaking at 50 psi H2 at ambient temperature for five hours, the mixture was filtered and the filtrate concentrated to an oil (4.2 g). This oil was eluted on a silica gel column with ethyl acetate via HPLC and the desired fractions were combined and concentrated to give a solid, 4.0 g, m.p. 89-90° C. This material was recrystallized from ether/hexanes (4:1) to give a solid, 2.9 g, m.p. 90°-92° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated to an oil (4.2 g)
  3. washThis oil was eluted on a silica gel column with ethyl acetate via HPLC
  4. concentrationconcentrated
  5. customto give a solid, 4.0 g, m.p. 89-90° C
  6. customThis material was recrystallized from ether/hexanes (4:1)
  7. customto give a solid, 2.9 g, m.p. 90°-92° C.

Sources & evidence

ORD record
ord-110968aa6cbd4fe8a2f717e45a67260f
Source dataset
uspto-grants-1991_08
Patent number
US05037835

Reaction notes

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