HCID 69432488, compound → HCID 69436371, compound

HRID 1269966Notes

Reaction equation

HRID 1269966 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]([CH:23]=[CH2:24])[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(OCC)(=O)C.[Pd]>[CH2:23]([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)[CH3:24]

Participants

4

Reactant 1

HCID 69432488HCID 69432488, compound

Product 1

HCID 69436371HCID 69436371, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-4-vinyl-1H-indazole (1.35 g, 4.11 mmol) in ethyl acetate (40 ml) was added 10%-palladium/carbon (containing 50% water, 50 mg), and the resulting mixture was stirred for 6 hours at ordinary temperature and atmospheric pressure under a hydrogen atmosphere. To the mixture was further added 10%-palladium/carbon (containing 50% water, 670 mg), and stirred for another 1.5 hours. 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 4-ethyl-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (1.41 g).

Workup

  1. stirringstirred for another 1.5 hours
  2. filtrationThe reaction mixture was filtered by the use of Celite
  3. washwashed with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-19320c3924e342fc969d8bd1b10d632e
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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