HCID 178526541, compound → HCID 178507437, compound

HRID 2065793Notes

Reaction equation

HRID 2065793 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[C:7]([C:9]3[N:14]=[C:13]([OH:15])[C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1>C(O)C>[NH2:16][C:12]1[C:13]([OH:15])=[N:14][C:9]([C:7]2[N:8]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[NH:5][C:6]=2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 178526541HCID 178526541, compound

Product 1

HCID 178507437HCID 178507437, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-[2-Cyclopropyl-5-(2,4-difluorophenyl)-1H-imidazol-4-yl]-3-nitro-pyridin-2-ol (4.525 g, 12.63 mmol) is dissolved in ethanol (63 mL). The solution is degassed with bubbling nitrogen gas. 10% Pd/C (920 mg) is added portionwise to the mixture and the mixture is saturated with hydrogen. The mixture is stirred under a hydrogen atmosphere (balloon) at RT over the weekend, at which time LC/MS shows complete conversion. The suspension is filtered through a pad of CELITE® to remove the catalyst and the solution is concentrated under reduced pressure to afford the title compound (3.97 g, 89%). LC-ES/MS m/z 328.9 (M+1).

Workup

  1. customThe solution is degassed with bubbling nitrogen gas
  2. addition10% Pd/C (920 mg) is added portionwise to the mixture
  3. filtrationThe suspension is filtered through a pad of CELITE®
  4. customto remove the catalyst
  5. concentrationthe solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-96507a19c298432f9c7b776a5ee7e608
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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