Water → HCID 18950394, compound

HRID 1492490Notes

Reaction equation

HRID 1492490 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](Br)=[C:17](Br)[N:18]3[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])[C:7]([C:10]([OH:12])=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Na+].[H][H].O>C(O)C.[OH-].[OH-].[Pd+2].CO>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])[C:7]([C:10]([OH:12])=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 962WaterHCID 18950372HCID 18950372, compoundHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178418361HCID 178418361, compound

Product 1

HCID 18950394HCID 18950394, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 2-butyl-1-[[2,3-dibromo-1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5carboxylic acid in ethanol (26 ml, 0.032M), sodium hydroxide water solution (1N, 2.923 ml, 2,923 mmol, 3.5 eq.), and palladium hydroxide on carbon (186 mg) were added. The mixture was placed under a balloon of hydrogen gas and stirred at room temperature. After 1.5 hours, 20 ml water and 40 ml methanol were added and the reaction was filtered. The filtrate was concentrated to about 20 ml and acidified with 1N HCl to pH~2. The mixture was extracted with 10% methanol in methylene chloride. The extract was washed with brine and concentrated. The residue was chromatographed on silica gel eluting with EtOAc: Pyridine:AcOH:H2O (40:1:1:0.5) to give the title B compound (200 mg).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationThe filtrate was concentrated to about 20 ml
  3. extractionThe mixture was extracted with 10% methanol in methylene chloride
  4. washThe extract was washed with brine
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with EtOAc: Pyridine:AcOH:H2O (40:1:1:0.5)

Sources & evidence

ORD record
ord-c69ac37618304c989bf536830d29c2f6
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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