HCID 178500118, compound → HCID 178500115, compound

HRID 2065785Notes

Reaction equation

HRID 2065785 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12]([C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[N:11][C:10]=1[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([OH:30])[N:22]=1>CO.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:10]2[N:11]=[C:12]([C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[NH:13][C:9]=2[C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[N:22][C:23]=1[OH:30]

Participants

4

Reactant 1

HCID 178500118HCID 178500118, compound

Product 1

HCID 178500115HCID 178500115, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-[5-(2,4-difluorophenyl)-4-(6-hydroxy-5-nitro-2-pyridyl)-1H-imidazol-2-yl]-2-methyl-propanoate (49.5 g, 118.32 mmol) and palladium 5% weight (dry basis) on activated carbon (4.95 g, 2.33 mmol) in methanol (1.18 L) is stirred under a hydrogen atmosphere (balloon) at RT overnight. The suspension is filtered through CELITE®, rinsed with methanol, and the filtrate is concentrated under reduced pressure to afford the crude title compound (39 g) as a brown solid.

Workup

  1. filtrationThe suspension is filtered through CELITE®
  2. washrinsed with methanol
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea5f8436cc3a437db1a12cfce991b328
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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