HCID 19603768, compound → HCID 19603746, compound

HRID 1604687Notes

Reaction equation

HRID 1604687 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19](=[O:40])[CH2:20][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([C:30]([O:32]CC5C=CC=CC=5)=[O:31])=[CH:22]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[OH-].[OH-].[Pd+2]>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19](=[O:40])[CH2:20][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([C:30]([OH:32])=[O:31])=[CH:22]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19603768HCID 19603768, compound

Product 1

HCID 19603746HCID 19603746, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 1-{2-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-oxoethyl}indole-3-carboxylate (140 mg) in tetrahydrofuran (4 ml) was hydrogenated over 10% Pd(OH)2 (22 mg) at room temperature under atmospheric pressure. After removal of the catalyst by filtration the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of dichloromethane and methanol. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 1-{2-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-oxoethyl}indole-3-carboxylic acid (90 mg).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration the filtrate
  3. concentrationwas concentrated under reduced pressure
  4. washeluted with a mixture of dichloromethane and methanol
  5. additionThe fractions containing the objective compound
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e4cd0b3ed9d949b18a9305d2af1fcabc
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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