HCID 10341046, compound → HCID 10250642, compound

HRID 2181228Notes

Reaction equation

HRID 2181228 reaction equation
[CH3:1][O:2]/[C:3](=[CH:7]\[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][CH2:18][C:19]1[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=1[CH3:24])[CH:12]=[CH:11]2)/[C:4]([OH:6])=[O:5].[H][H]>CO.ClCCl.[Pd]>[CH3:1][O:2][CH:3]([CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][CH2:18][C:19]1[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=1[CH3:24])[CH:12]=[CH:11]2)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 2

HCID 10341046HCID 10341046, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10250642HCID 10250642, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 9 mg of (Z)-2-Methoxy-3-{1-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl]-1H-indol-5-yl}-acrylic acid in 2 ml of methanol and 1 ml of dichloromethane and 6 mg of Pd/C 10%) was hydrogenated at 22° C. and 1 bar until hydrogen uptake ceased (2 h). The mixture was filtered, the filtrate evaporated and the residue was purified by HPLC (RP-18, CH3CN/H2O, gradient) to give 7 mg of the title compound as a colorless oil. MS: (M−H)− 403.3.

Workup

  1. customwas hydrogenated at 22° C.
  2. custom(2 h)
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customthe residue was purified by HPLC (RP-18, CH3CN/H2O, gradient)

Sources & evidence

ORD record
ord-0cdbfa361e924493b8344f795539294a
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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