1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(5-methyl-2-styryl-oxazol-4-ylmethyl)-2,3-dihydro-1H-indol-5-yl]-propan-2-ol → 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(5-methyl-2-phenethyl-oxazol-4-ylmethyl)-2,3-dihydro-1H-indol-5-yl]-propan-2-ol

HRID 1724052Notes

Reaction equation

HRID 1724052 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[N:20]=[C:21]([CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:22][C:23]=1[CH3:24])[CH:13]([CH3:33])[CH2:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5]>CO.[Pd]>[F:6][C:4]([F:5])([F:7])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[N:20]=[C:21]([CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:22][C:23]=1[CH3:24])[CH:13]([CH3:33])[CH2:12]2)([OH:8])[C:2]([F:35])([F:34])[F:1]

Participants

4

Reactant 1

HCID 737412221,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(5-methyl-2-styryl-oxazol-4-ylmethyl)-2,3-dihydro-1H-indol-5-yl]-propan-2-ol

Product 1

HCID 210821661,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(5-methyl-2-phenethyl-oxazol-4-ylmethyl)-2,3-dihydro-1H-indol-5-yl]-propan-2-olYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 30 mg (0.06 mmol) of 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(5-methyl-2-styryl-oxazol-4-ylmethyl)-2,3-dihydro-1H-indol-5-yl]-propan-2-ol (example 136) in 1 ml of methanol was treated with 15 mg of Pd/C (10%) and stirred under H2 at atmospheric pressure for 6 hours. Filtration and evaporation of the solvent gave 24 mg (77%) of 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(5-methyl-2-phenethyl-oxazol-4-ylmethyl)-2,3-dihydro-1H-indol-5-yl]-propan-2-ol, light yellow oil, MS: 499 (MH+).

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-935610f3a25d44fe8fcf15746bef0cfc
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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