Sodium periodate → HCID 123895025, compound

HRID 1056991Notes

Reaction equation

HRID 1056991 reaction equation
[F:1][C:2]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:3]=1[O:4][C:5]1[C:13]2[N:12]=[CH:11][N:10]([CH3:14])[C:9]=2[C:8]([CH:15]=C)=[CH:7][C:6]=1[C:17]1[C:18]2[CH:27]=[N:26][N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:19]=2[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=1.I([O-])(=O)(=O)=[O:42].[Na+]>O.O1CCCC1.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:3]=1[O:4][C:5]1[C:13]2[N:12]=[CH:11][N:10]([CH3:14])[C:9]=2[C:8]([CH:15]=[O:42])=[CH:7][C:6]=1[C:17]1[C:18]2[CH:27]=[N:26][N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:33])[CH3:34])[C:19]=2[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 123458513HCID 123458513, compound

Product 1

HCID 123895025HCID 123895025, compoundYield 68.8%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-[4-(2,4-difluorophenoxy)-1-methyl-7-vinyl-1H-benzimidazol-5-yl]-6-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one (0.076 g, 0.13 mmol) and sodium metaperiodate (0.0865 g, 0.404 mmol) in water (0.23 mL) and tetrahydrofuran (3.10 mL) was treated with 0.16M solution of osmium tetraoxide in water (0.172 mL, 0.0270 mmol). The resultant reaction mixture was stirred at 60° C. for 30 min. The reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give a crude residue. Purification by flash column chromatography (100% hexanes to 100% EtOAc [EtOAc contained 5% MeOH]) gave the desired product (50.6 mg, 66%). LCMS calculated for C28H30F2N5O4Si (M+H)+: m/z=566.2. found: 566.1.

Workup

  1. customThe resultant reaction mixture
  2. customLayers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude residue
  8. customPurification by flash column chromatography (100% hexanes to 100% EtOAc [EtOAc contained 5% MeOH])

Sources & evidence

ORD record
ord-4fead46cf92d4370af06b360b979d76b
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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