HCID 136340694, compound → HCID 178509098, compound

HRID 570968Notes

Reaction equation

HRID 570968 reaction equation
[N+:1]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)([O-])=O>[Pd].CO>[S:12]1[CH:13]=[CH:14][CH:15]=[C:11]1/[CH:10]=[CH:9]/[C:5]1[N:6]=[CH:7][NH:8][C:4]=1[NH2:1]

Participants

4

Reactant 1

HCID 136340694HCID 136340694, compound

Product 1

HCID 178509098HCID 178509098, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Palladium on carbon (0.5 g) was added to a solution of (E)-5-nitro-4-(2-(thiophen-2-yl)vinyl)-1H-imidazole (4.5 g, 0.02 mol) in methanol (500 mL) and the resulting mixture hydrogenated at atmospheric pressure for 24 hours. The catalyst was removed by filtering through a short bed of Celite™, and the Celite™ washed with 10% MeOH/DCM (200 mL). The filtrate was evaporated to dryness and purified by column chromatography (5-10% MeOH/DCM) to leave the product as a pale brown solid (2.75 g, 71%). δH (DMSO-d6) 11.58 (1H, bs, NH), 7.25 (2H, m), 6.95 (3H, m), 6.62 (1H, d, J=16.0), 4.86 (2H, bs, NH2).

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through a short bed of Celite™
  3. washthe Celite™ washed with 10% MeOH/DCM (200 mL)
  4. customThe filtrate was evaporated to dryness
  5. custompurified by column chromatography (5-10% MeOH/DCM)

Sources & evidence

ORD record
ord-e3aa2ad6483f49d0a6e079e45f14254c
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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