5-(Benzyloxy)-6-(6-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → 6-(6-Methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-ol

HRID 2195516Notes

Reaction equation

HRID 2195516 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[C:18]1[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=1)[N:14]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[N:13]=[CH:12]2)C1C=CC=CC=1>CCO.CCOC(C)=O.[Pd]>[CH3:24][C:21]1[N:20]=[CH:19][C:18]([C:17]2[CH:16]=[C:15]3[C:11]([CH:12]=[N:13][N:14]3[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)=[CH:10][C:9]=2[OH:8])=[CH:23][CH:22]=1

Participants

5

Reactant 1

HCID 667671245-(Benzyloxy)-6-(6-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 667672706-(6-Methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-olYield 88.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(benzyloxy)-6-(6-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.44 g, 3.60 mmol) in EtOH (50 mL) and EtOAc (50 mL) is added Pd/C (500 mg, 10% wt) under N2. The resulting mixture is degassed by evacuation and backfilled with nitrogen. Then the reaction mixture is stirred at RT under H2 atmosphere overnight. The reaction mixture is filtered. The filtrate is concentrated to give the product (982 mg, 88.0% yield). MS (m/z): 310.1 (M+H).

Workup

  1. customThe resulting mixture is degassed by evacuation
  2. filtrationThe reaction mixture is filtered
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-788946eb1a4f47b098e2161c4c6bdd7a
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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