HCID 69433897, compound → HCID 69434565, compound

HRID 1269968Notes

Reaction equation

HRID 1269968 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[C:11]([C:23](O)([CH3:25])[CH3:24])[C:12]([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1>C(O)C.[Pd]>[CH:23]([C:11]1[C:12]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[N:8][N:7]2[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([CH3:25])[CH3:24].[CH:23]([C:11]1[C:12]([OH:16])=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[N:8][N:7]2[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([CH3:25])[CH3:24]

Participants

5

Reactant 1

HCID 69433897HCID 69433897, compound

Product 2

HCID 69430803HCID 69430803, compoundYield 16%HCID 69434565HCID 69434565, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In an autoclave, 10%-palladium/carbon (containing 50% water, 1.0 g) was added to a solution of 2-[1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazol-4-yl]propan-2-ol (1.92 g, 5.33 mmol) in ethanol (26 ml), and the resulting mixture was stirred at 60° C. for 5 hours under a hydrogen atmosphere of 30 atmospheric pressure. The reaction mixture was filtered by the use of Celite and washed with methanol, and then the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-isopropyl-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (301 mg, 16%) and 4-isopropyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-ol (586 mg, 42%).

Workup

  1. filtrationThe reaction mixture was filtered by the use of Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain a crude product
  5. customThe crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a4833bcb346346138b13f7fe13982da4
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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