2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-1H-indol-5-yl]-propan-2-ol

HRID 1724025Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:19][OH:20])[CH:13]([CH3:27])[CH2:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5].O1CCOCC1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[NH4+].[Cl-]>C1(C)C=CC=CC=1.O=[Mn]=O.CCOCC>[F:29][C:2]([F:1])([F:28])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:19][OH:20])[C:13]([CH3:27])=[CH:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 40 mg (0.094 mmol) 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-2,3-dihydro-1H-indol-5-yl]-propan-2-ol (example 70) in 1 mL of toluene was treated with 45 mg (0.47 mmol) of MnO2. After stirring at 80° C. for 8 hrs, 0.5 mL of dioxane and 22 mg (0.094 mmol) of DDQ were added. The resulting mixture was stirred at RT overnight and poured into a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 2:1 yielded 15 mg (38%) of 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-1H-indol-5-yl]-propan-2-ol, brown oil, MS: 418 (MH+).

Workup

stirringThe resulting mixture was stirred at RT overnight
customThe phases were separated
extractionthe aqueous one was extracted with Et2O
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-a49c9af9f4db41ea94689e875de3ca7b
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485652B2

Reaction notes

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