HCID 68589822, compound → HCID 59314127, compound

HRID 1047798Notes

Reaction equation

HRID 1047798 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[CH2:7][C:6]([NH:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[CH:24]=[CH:25][CH3:26])([C:12]([OH:14])=[O:13])[CH2:5]2>CCO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[CH2:7][C:6]([NH:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[CH2:24][CH2:25][CH3:26])([C:12]([OH:14])=[O:13])[CH2:5]2

Participants

4

Reactant 1

HCID 68589822HCID 68589822, compound

Product 1

HCID 59314127HCID 59314127, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5,6-Difluoro-2-[3-methyl-2-(-propenyl)-benzoylamino]-indan-2-carboxylic acid (160) (110 mg, 0.30 mmol) is dissolved in absolute EtOH (15 mL) by heating. The resulting solution is cooled to RT and catalyst, Pd—C (5 wt. % Pd, 64 mg, 3.0% mmol) is added under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 55 psi, 50° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined EtOH solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (161) as white solid (80 mg, 71%).

Workup

  1. temperatureby heating
  2. customThe resulting reaction mixture
  3. custom55 psi, 50° C., overnight
  4. customThe catalyst is removed by filtration through a pre-column (10 g silica gel)
  5. washwashed with EtOH
  6. concentrationThe combined EtOH solution is concentrated in vacuo
  7. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-f396e300034a4ea59f30705abe38f636
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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