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 1662000Notes

Reaction equation

HRID 1662000 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-2df150b927da41ff9120a366eb031085
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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