Tetrahydrofuran → HCID 69430532, compound

HRID 1269988Notes

Reaction equation

HRID 1269988 reaction equation
[CH3:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCCC1>ClCCl>[CH3:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 229335464-methyl-1H-indazol-5-ol

Product 1

HCID 69430532HCID 69430532, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, the 4-methyl-1H-indazol-5-ol (500 mg, 3.37 mmol) obtained in Example 402 was suspended in dichloromethane (20 ml), followed by adding thereto 3,4-dihydro-2H-pyran (239 μl, 3.71 mmol) and p-toluenesulfonic acid monohydrate (64 mg, 0.337 mmol). Tetrahydrofuran (25 ml) was added thereto to effect dissolution, and the reaction was carried out at room temperature for 2 days. The solvent was distilled off under reduced pressure and water was added to the residue, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to obtain 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-ol (477 mg, yield 60.9%).

Workup

  1. additionby adding
  2. dissolutiondissolution
  3. distillationThe solvent was distilled off under reduced pressure and water
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried by the addition of anhydrous magnesium sulfate
  8. filtrationfiltered
  9. distillationThe solvent was distilled off under reduced pressure
  10. concentrationthe resulting concentration residue
  11. customwas purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-df977e6bc0314dff8147c34f9f8d8afe
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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