Ethanol → 5-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047795Notes

Reaction equation

HRID 1047795 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1/[CH:23]=[CH:24]/[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2.[CH3:27]CO>[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[CH2:23][CH:24]([CH3:27])[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2

Participants

4

Reactant 2

HCID 702EthanolHCID 251608005-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid

Product 1

HCID 251606695-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

5-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid (154) (270 mg, 0.76 mmol) is dissolved in absolute EtOH (15 mL) by heating. The resulting solution is cooled down to RT under argon and then is added the catalyst, Pd—C (5 wt. % Pd, 125 mg, 5.9% mmol). The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, 50° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (155) as white solid (210 mg, 78%).

Workup

  1. temperatureby heating
  2. customThe resulting reaction mixture
  3. custom50 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 organic solution is concentrated in vacuo
  7. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-81549fef3bc04928a16d129eaefd0dfb
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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