HCID 10296528, compound → HCID 18003554, compound

HRID 479155Notes

Reaction equation

HRID 479155 reaction equation
[CH2:1]([O:3]/[C:4](=[CH:8]\[C:9]1[C:17]2[O:16][CH:15]=[CH:14][C:13]=2[C:12]([O:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[CH:11][CH:10]=1)/[C:5]([OH:7])=[O:6])[CH3:2]>CO.C(Cl)Cl.[Pd]>[CH2:1]([O:3][CH:4]([CH2:8][C:9]1[C:17]2[O:16][CH2:15][CH2:14][C:13]=2[C:12]([O:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:24][C:25]=2[CH3:26])=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 1

HCID 10296528HCID 10296528, compound

Product 1

HCID 18003554HCID 18003554, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 100 mg of 2Z-ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzofuran-7-yl}-acrylic acid and 25 mg of Pd/C (10%) in 2 ml of MeOH and 2 ml of CH2Cl2 was hydrogenated at 22° C./1bar overnight. The suspension was filtered and the filtrate was again hydrogenated with 25 mg of fresh catalyst overnight. The suspension was filtered, the filtrate evaporated and the residue purified by prep. HPLC (RP-18, CH3CN/H2O, gradient) to give the title compound (56 mg, 56%) as a pale yellow solid.

Workup

  1. customwas hydrogenated at 22° C.
  2. custom1bar overnight
  3. filtrationThe suspension was filtered
  4. customwas again hydrogenated with 25 mg of fresh catalyst overnight
  5. filtrationThe suspension was filtered
  6. customthe filtrate evaporated
  7. customthe residue purified by prep

Sources & evidence

ORD record
ord-faaf1d339d45430992806b913492cd93
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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