HCID 67057742, compound → HCID 67057753, compound

HRID 604636Notes

Reaction equation

HRID 604636 reaction equation
[F:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH3:20])=[CH:16][CH2:17]3)=[CH:13][C:12]=2[C:21]([O:23][CH3:24])=[O:22])=[C:4]([O:25][CH3:26])[CH:3]=1>CCO.[Pd]>[F:1][C:2]1[C:7]([CH:8]([CH3:9])[CH3:10])=[CH:6][C:5]([C:11]2[CH:19]=[C:18]3[C:14]([CH:15]([CH3:20])[CH2:16][CH2:17]3)=[CH:13][C:12]=2[C:21]([O:23][CH3:24])=[O:22])=[C:4]([O:25][CH3:26])[CH:3]=1

Participants

4

Reactant 1

HCID 67057742HCID 67057742, compound

Product 1

HCID 67057753HCID 67057753, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 6-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3-methyl-1H-indene-5-carboxylate (21.5 mg, 0.061 mmol) in EtOH (2 mL), was added a catalytic amount of 10% Pd/C. The flask was stirred at room temperature under H2 overnight. The mixture was filtered through Celite. The solvent was evaporated in vacuo to give methyl 6-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3-methylindane-5-carboxylate. LCMS calc.=379.2; found=378.9 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 7.72 (s, 1H); 7.18 (s, 1H); 7.11 (d, J=8.6 Hz, 1H); 6.62 (d, J=12.0 Hz, 1H); 3.73 (s, 3H); 3.69 (s, 3H); 3.29-3.23 (m, 2H); 3.02-2.90 (m, 2H); 2.45-2.34 (m, 1H); 1.73-1.66 (m, 1H); 1.38 (d, J=6.2 Hz, 3H); 1.30 (d, J=6.6 Hz, 6H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-aa719ddd2dc84b34ab25b00bb29d0572
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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