(Z)-2-Methoxy-3-[1-(5-methyl-2-phenyl-oxazol-4-ylmethyl)-1H-indol-5-yl]-acrylic Acid → 2-methoxy-3-(1-((5-methyl-2-phenyloxazol-4-yl)methyl)-1H-indol-5-yl)propanoic acid

HRID 2181227Notes

Reaction equation

HRID 2181227 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][C:18]1[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=1[CH3:23])[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][C:18]1[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=1[CH3:23])[CH:12]=[CH:11]2)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 2

HCID 11740979(Z)-2-Methoxy-3-[1-(5-methyl-2-phenyl-oxazol-4-ylmethyl)-1H-indol-5-yl]-acrylic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 100232792-methoxy-3-(1-((5-methyl-2-phenyloxazol-4-yl)methyl)-1H-indol-5-yl)propanoic acidYield 60.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 80 mg of (Z)-2-methoxy-3-[1-(5-methyl-2-phenyl-oxazol-4-ylmethyl)-1H-indol-5-yl]-acrylic acid in 5 ml of methanol and 2 ml of dichloromethane and 30 mg of Pd/C 10%) was hydrogenated at 22° C. and 1 bar until hydrogen uptake ceased (3 h). The mixture was filtered, the filtrate evaporated and the residue was purified by preparative HPLC (RP-18, CH3CN/H2O, gradient) to give 49 mg of the title compound as a yellow oil. MS: (M−H)− 389.1.

Workup

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

Sources & evidence

ORD record
ord-bccd3efc8dcc4ae990a626f670b26875
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

Loading…