HCID 21082173, compound → HCID 135848759, compound

HRID 346858Notes

Reaction equation

HRID 346858 reaction equation
[F:1][C:2]([F:41])([F:40])[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]([C:25]3[CH:30]=[CH:29][C:28]([O:31]CC4C=CC=CC=4)=[CH:27][CH:26]=3)[O:22][C:23]=1[CH3:24])[C:13]([CH3:39])=[CH:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5]>CO.[Pd]>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[N:20][C:19]=1[CH2:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:41])([F:40])[F:1])[C:4]([F:5])([F:6])[F:7])=[CH:17][CH:16]=2)[CH:12]=[C:13]1[CH3:39]

Participants

4

Reactant 1

HCID 21082173HCID 21082173, compound

Product 1

HCID 135848759HCID 135848759, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 80 mg (0.139 mmol) of 2-{1-[2-(4-benzyloxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 98) in 1 mL of methanol was treated with 20 mg Pd/C (10% Pd) and stirred under H2 at atmospheric pressure for 6 hrs. Filtration and evaporation of the solvent yielded 59 mg (87%) of 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-oxazol-2-yl}-phenol, light green foam, MS: 485 (MH+).

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-7cdfed61393445caaa2872dbeb44f04a
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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