Dimethyl Sulfoxide → 6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbaldehyde

HRID 1827460Notes

Reaction equation

HRID 1827460 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][OH:18])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:4][CH:3]=1.CS(C)=O>CCOC(C)=O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:17]=[O:18])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 22136538[6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazol-3-yl]-methanol

Product 1

HCID 221365606-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazol-3-yl]-methanol (1.75 g, 6.58 mmol), IBX (2.76 g, 9.87 mmol) and DMSO (27 mL) was stirred overnight. The reaction was diluted in EtOAc and water. The layers were separated, and the aqueous was extracted with EtOAc (3×100 mL). The organics were combined and washed with saturated NaCl (100 mL). The organic was dried over MgSO4, filtered, and then concentrated to a solid. The solid was dissolved in CH2Cl2, and filtered. The organic was evaporated to yield the desired product (1.707 g, 92%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with EtOAc (3×100 mL)
  3. washwashed with saturated NaCl (100 mL)
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. dissolutionThe solid was dissolved in CH2Cl2
  8. filtrationfiltered
  9. customThe organic was evaporated

Sources & evidence

ORD record
ord-351d824f6538412aa306223e03e08d50
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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