Trifluoroacetic acid → 4-nitro-1-(piperidin-3-ylmethyl)-1H-indazole

HRID 706713Notes

Reaction equation

HRID 706713 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)([O-:3])=[O:2].FC(F)(F)C(O)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699345tert-butyl 3-((4-nitro-1H-indazol-1-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 679761024-nitro-1-(piperidin-3-ylmethyl)-1H-indazoleYield 126.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-((4-nitro-1H-indazol-1-yl)methyl)piperidine-1-carboxylate (0.118 g, 0.327 mmol) in DCM (1.6 mL) was treated with trifluoroacetic acid (0.4 mL) at ambient temperature and stirring continued for 2 hours. The solvent was concentrated and the resulting gum was dried under high vacuum to afford 4-nitro-1-(piperidin-3-ylmethyl)-1H-indazole (0.108 g, 92% yield) as a brown oil.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe resulting gum was dried under high vacuum

Sources & evidence

ORD record
ord-96f69d6974a64d3a8baf64a2f2a5c715
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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