Water → HCID 178519378, compound

HRID 591689Notes

Reaction equation

HRID 591689 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][OH:19])[CH:16]=2)[NH:11][N:10]=1.O>CS(C)=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[O:19])[CH:16]=2)[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 178519379HCID 178519379, compound

Product 1

HCID 178519378HCID 178519378, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of [3-(tetrahydro-pyran-2-yloxymethyl)-1H-indazol-5-yl]-methanol (0.40 g, 1.50 mmol) in DMSO (3 mL), IBX (0.42 g, 1.50 mmol) was added and the reaction mixture was stirred at room temperature for 3 hours under nitrogen. Water (50 mL) was added; the separated solid was filtered, and the solid was washed with ethyl acetate (100 mL). The filtrate was collected and the organic phase was separated, washed with brine (100 mL), and dried over anhydrous Na2SO4. Removal of solvent gave 3-(tetrahydro-pyran-2-yloxymethyl)-1H-indazole-5-carbaldehyde as an off-white solid. Yield: 0.33 g (84%).

Workup

  1. filtrationthe separated solid was filtered
  2. washthe solid was washed with ethyl acetate (100 mL)
  3. customThe filtrate was collected
  4. customthe organic phase was separated
  5. washwashed with brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-e732e1e74bbc4802a0ae9e94e98109f0
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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