HCID 67814469, compound → HCID 86666722, compound

HRID 2401381Notes

Reaction equation

HRID 2401381 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:24])=[N:12][CH:13]=[CH:14][C:15]=1[C:16]1[C:17]([CH3:23])=[N:18][O:19][C:20]=1[CH2:21][OH:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:24])=[N:12][CH:13]=[CH:14][C:15]=1[C:16]1[C:17]([CH3:23])=[N:18][O:19][C:20]=1[CH:21]=[O:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67814469HCID 67814469, compound

Product 1

HCID 86666722HCID 86666722, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (4-(3-((tert-butyldimethylsilyloxy)methyl)-2-fluoropyridin-4-yl)-3-methylisoxazol-5-yl)methanol (1.35 mg, 8.83 mmol) in CH2Cl2 (38 mL) at room temperature was added manganese dioxide (6.66 g, 77 mmol). The heterogeneous reaction was heated to 50° C. in a sealed tube for 2 h. The reaction was then cooled to room temperature and filtered. Then the solid was rinsed with EtOAc and the filtrate was concentrated to dryness under vacuum. The residue was used without any purification in the next step. LC/MS m/z 351 [M−H]+.

Workup

  1. customThe heterogeneous reaction
  2. temperatureThe reaction was then cooled to room temperature
  3. filtrationfiltered
  4. washThen the solid was rinsed with EtOAc
  5. concentrationthe filtrate was concentrated to dryness under vacuum
  6. customThe residue was used without any purification in the next step

Sources & evidence

ORD record
ord-60b25e6befa24b609f4b69314cb06b14
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…