1-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-cyclopropyl-4-nitro-1H-indazole → HCID 67251409, compound

HRID 79484Notes

Reaction equation

HRID 79484 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([N+:26]([O-])=O)[CH:22]=[CH:23][CH:24]=3)[C:19]([CH:29]3[CH2:31][CH2:30]3)=[N:18]2)=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1>CCO.[Pd]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[C:19]([CH:29]1[CH2:31][CH2:30]1)=[N:18][N:17]2[CH2:16][C:12]1[N:13]=[C:14]([CH3:15])[C:9]([OH:8])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 672611071-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-cyclopropyl-4-nitro-1H-indazole

Product 1

HCID 67251409HCID 67251409, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 1-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-cyclopropyl-4-nitro-1H-indazole (5.1 g, 12.3 mmol) in EtOH (100 mL) was carefully added Pd/C (10%, 1.5 g, 1.41 mmol). The reaction mixture was evacuated with N2 and H2 (three times each), and stirred under a H2 balloon for 3 hours. The reaction mixture was then evacuated with N2, filtered through Celite® and washed with MeOH. The filtrate was concentrated to give the desired product (86%) which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was evacuated with N2 and H2 (three times each), and
  2. customThe reaction mixture was then evacuated with N2
  3. filtrationfiltered through Celite®
  4. washwashed with MeOH
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eb369a6e67244ee3b7513b863754c3b5
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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