HCID 21082156, compound → HCID 21082219, compound

HRID 346869Notes

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]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=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]>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:26]=[CH:27][C:28]([CH:31]=[O:32])=[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:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:34])[F:35])=[CH:17][CH:16]=2)[CH:12]=[C:13]1[CH3:33]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 100 mg (0.2 mmol) of 1,1,1,3,3,3-hexafluoro-2-{1-[2-(4-hydroxymethyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-propan-2-ol in 2 ml of toluene was treated with 87 mg (1.0 mmol) of MnO2 and stirred at 80° C. during 20 hours. Filtration, evaporation of the solvent and chromatography on silica gel with heptane/EtOAc 4:1 gave 50 mg (50%) of 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-oxazol-2-yl}-benzaldehyde, pink solid, MS: 497 (MH+).

Workup

filtrationFiltration, evaporation of the solvent and chromatography on silica gel with heptane/EtOAc 4:1

Sources & evidence

ORD record: ord-aa6d7a8a096e4fb29686976d36557b0d
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173048B2

Reaction notes

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