4-Nitroindazole → tert-butyl 3-((4-nitro-1H-indazol-1-yl)methyl)piperidine-1-carboxylate

HRID 706712Notes

Reaction equation

HRID 706712 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].[H-].[Na+].S(O[CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]1)(C1C=CC(C)=CC=1)(=O)=O>CC(N(C)C)=O.O>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:28]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 180574-NitroindazoleHCID 24758Sodium hydrideHCID 18369320Tert-butyl 3-((P-tolylsulfonyloxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86699345tert-butyl 3-((4-nitro-1H-indazol-1-yl)methyl)piperidine-1-carboxylateYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-nitro-1H-indazole (0.200 g, 1.23 mmol) in DMA (3 mL) was added 60% sodium hydride (0.074 g, 1.84 mmol) at ambient temperature. After 30 minutes, tert-butyl 3-(tosyloxymethyl)piperidine-1-carboxylate (0.544 g, 1.47 mmol) was added. The mixture was heated at 100° C. overnight, diluted with water, extracted with DCM, dried (phase separator silicone treated filter paper), concentrated and the residue purified on silica gel (10-50% EtOAc in DCM) to provide tert-butyl 3-((4-nitro-1H-indazol-1-yl)methyl)piperidine-1-carboxylate (0.176 g, 40% yield) as a yellow gum.

Workup

  1. extractionextracted with DCM
  2. customdried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated
  5. customthe residue purified on silica gel (10-50% EtOAc in DCM)

Sources & evidence

ORD record
ord-c248d80cb09c401bbf4e079f1f9b4120
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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