HCID 25160921, compound → HCID 25160920, compound

HRID 1047797Notes

Reaction equation

HRID 1047797 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:28])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[CH:24]=[C:25]([CH3:27])[CH3:26])([C:12]([OH:14])=[O:13])[CH2:5]2>C(O)(=O)C.[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:28])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[CH2:24][CH:25]([CH3:26])[CH3:27])([C:12]([OH:14])=[O:13])[CH2:5]2

Participants

4

Reactant 1

HCID 25160921HCID 25160921, compound

Product 1

HCID 25160920HCID 25160920, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5,6-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid (158) (200 mg, 0.63 mmol) is dissolved in acetic acid (15 mL) by heating. The resulting solution is cooled down to RT and then the catalyst, Pd—C (5 wt. % Pd, 134 mg, 6.3% mmol) is added under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 55 psi, 95° 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 (159) as white solid (170 mg, 84%).

Workup

  1. temperatureby heating
  2. customThe resulting reaction mixture
  3. custom55 psi, 95° 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-edeb18705df2472da18b72d61a15eb90
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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