HCID 11966965, compound → HCID 9803861, compound

HRID 129566Notes

Reaction equation

HRID 129566 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([OH:16])=[O:15])=[C:6]1[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[N:32]=[N:33][N:34](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:35]=2)=[CH:21][CH:20]=1)O)[CH2:2][CH2:3][CH3:4]>[Pd].C(O)(=O)C.C1COCC1>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([OH:16])=[O:15])=[C:6]1[CH2:17][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[N:32]=[N:33][NH:34][N:35]=2)=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 11966965HCID 11966965, compound

Product 1

HCID 9803861HCID 9803861, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-butyl-2-{2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-biphenyl-4-yl(hydroxy)methyl}-1H-indole-3-carboxylic acid (2.5 g, 3.52 mmol) and 10% palladium on carbon (1.2 g) in 20 mL of acetic acid and 80 mL of THF under a hydrogen atmosphere (200 psi) at 48° C. for approximately 48 hours. The mixture was then cooled, filtered and diluted with 500 mL of water. The mixture was extracted with 100 mL of ethyl acetate and the ethyl acetate layer was washed three times with water. The ethyl acetate layer was concentrated to give 1-butyl-2-[2'-(2H-tetrazol-5-yl)biphenyl-4-ylmethyl]-1H-indole-3-carboxylic acid (1.2 g, 2.66 mmol).

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered
  3. additiondiluted with 500 mL of water
  4. extractionThe mixture was extracted with 100 mL of ethyl acetate
  5. washthe ethyl acetate layer was washed three times with water
  6. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-01522e81a45b4dc8b73b21c88194b9a7
Source dataset
uspto-grants-1995_11
Patent number
US05468867

Reaction notes

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