HCID 67981122, compound → 1183808-98-1

HRID 1520006Notes

Reaction equation

HRID 1520006 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=1)([O-])=O>CO.[Pd]>[N:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 67981122HCID 67981122, compound

Product 1

HCID 608928391183808-98-1Yield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[2-(4-nitro-1H-pyrazol-1-yl)ethyl]pyridine (9.9 g; 34 mmol; 1.0 eq.) in MeOH (250 mL) in presence of a catalytic amount of Pd/C was hydrogenated under 14 bars of H2 at RT. After completion, the reaction mixture was filtered through a celite pad and concentrated. The crude was purified by flash chromatography on silica (DCM:MeOH, gradient from 100:0 to 80:20) to afford the title compound as a brown solid (3.26 g, 51%). MS (ESI+): 189.0 (purity 87.9%). 1H NMR (400 Mz, DMSO-d6) δ 842-8.41 (d, J=5.9 Hz, 2H), 7.15-7.14 (d, J=5.8 Hz, 2H), 6.96 (s, 1H), 6.91 (s, 1H), 4.21-4.19 (t, J=7.4 Hz, 2H), 3.99 (brs, 2H), 3.05-3.03 (t, J=7.1 Hz, 2H, t).

Workup

  1. customwas hydrogenated under 14 bars of H2 at RT
  2. filtrationAfter completion, the reaction mixture was filtered through a celite pad
  3. concentrationconcentrated
  4. customThe crude was purified by flash chromatography on silica (DCM:MeOH, gradient from 100:0 to 80:20)

Sources & evidence

ORD record
ord-82cb410addf142d1aecb62208e836bfc
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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